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<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">As filed with the
Securities and Exchange Commission on February&nbsp;9, 2005</font></p>

<p style="margin:0in 0in .0001pt;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="margin:0in 0in .0001pt 4.5in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">Registration
No. 333-</font></b></p>

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<p style="border:none;margin:0in 0in .0001pt;padding:0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

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<p style="border:none;font-weight:bold;margin:0in 0in .0001pt;padding:0in;page-break-after:auto;text-align:center;text-transform:uppercase;"><b><font size="5" face="Times New Roman" style="font-size:18.0pt;text-transform:none;">UNITED
STATES<br>
SECURITIES AND EXCHANGE COMMISSION</font></b></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">Washington, D.C.&#160;
20549</font></b></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="1" width="25%" noshade color="black" align="center">

</font></div>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-transform:uppercase;"><b><font size="5" face="Times New Roman" style="font-size:18.0pt;text-transform:none;">FORM S-8</font></b></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-transform:uppercase;"><b><font size="3" face="Times New Roman" style="font-size:12.0pt;text-transform:none;">REGISTRATION STATEMENT</font></b></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-transform:uppercase;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;text-transform:none;">&nbsp;</font></b></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="3" face="Times New Roman" style="font-size:12.0pt;font-weight:bold;">UNDER</font></b></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="3" face="Times New Roman" style="font-size:12.0pt;font-weight:bold;">THE SECURITIES ACT OF 1933</font></b></p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

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<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-transform:uppercase;"><b><font size="5" face="Times New Roman" style="font-size:18.0pt;text-transform:none;">OPTIONSXPRESS HOLDINGS, INC.</font></b></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;page-break-after:auto;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">(Exact name of registrant as
specified in its charter)</font></b></p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<table border="0" cellspacing="0" cellpadding="0" width="100%" style="border-collapse:collapse;width:100.0%;">
 <tr>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">Delaware</font></b>&nbsp;</p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">20-1444525</font></b>&nbsp;</p>
  </td>
 </tr>
 <tr>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(State or other jurisdiction of<br>
  incorporation or organization) </font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(I.R.S. Employer<br>
  Identification No.) </font></p>
  </td>
 </tr>
 <tr>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">39 South LaSalle Street, Suite 220</font></b><br>
  <b><font style="font-weight:bold;">Chicago, Illinois 60603</font></b>&nbsp;</p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="49%" valign="bottom" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">60603</font></b>&nbsp;</p>
  </td>
 </tr>
 <tr>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(Address of Principal Executive Offices)</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="49%" valign="top" style="padding:0in 0in 0in 0in;width:49.0%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(Zip Code)</font></p>
  </td>
 </tr>
</table>

<p style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;"><br>
2001 Equity Incentive Plan<br>
2005 Equity Incentive Plan <br>
2005 Employee Stock Purchase Plan<br>
</font></b>(Full titles of the plans)</p>

<p style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">David S. Kalt, Chief Executive Officer<br>
optionsXpress Holdings, Inc.<br>
39 South LaSalle Street, Suite 220<br>
Chicago, Illinois 60603<br>
</font></b>&#160;(Name and address of
agent for service)</p>

<p style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">(312) 630-3300<br>
</font></b>(Telephone number, including area code, of agent for service)</p>

<p style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-size:10.0pt;margin:0in 0in .0001pt;text-align:center;"><u><font size="2" face="Times New Roman" style="font-size:10.0pt;">Copy to</font></u>:<br>
<b><font style="font-weight:bold;">Sanford E. Perl, P.C.<br>
Gerald T. Nowak<br>
Kirkland &amp; Ellis LLP<br>
200 E. Randolph Drive<br>
Chicago, Illinois 60601<br>
Telephone: (312) 861-2000<br>
Telecopy: (312) 861-2200<br><br></font></b></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">CALCULATION OF REGISTRATION FEE<br><br></font></b></p>

<table border="0" cellspacing="0" cellpadding="0" width="100%" style="border-collapse:collapse;width:100.0%;">
 <tr>
  <td width="21%" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:21.88%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Title of securities to be<br>
  registered</font></b></p>
  </td>
  <td width="1%" valign="bottom" style="padding:0in 0in 0in 0in;width:1.96%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="16%" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:16.16%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Amount to be<br>
  registered (1)</font></b></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="16%" colspan="2" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:16.28%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Proposed maximum<br>
  offering price per<br>
  share</font></b></p>
  </td>
  <td width="3%" valign="bottom" style="padding:0in 0in 0in 0in;width:3.04%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="17%" colspan="2" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:17.34%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Proposed maximum<br>
  aggregate offering<br>
  price</font></b></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="17%" colspan="2" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:17.34%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Amount of<br>
  registration<br>
  fee</font></b></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="21%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:21.88%;">
  <p style="margin:0in 0in .0001pt 10.0pt;text-indent:-10.0pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Common Stock, par value $0.0001 per share</font></p>
  </td>
  <td width="1%" valign="bottom" style="padding:0in 0in 0in 0in;width:1.96%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="16%" valign="bottom" style="border:none;padding:0in 0in 0in 0in;width:16.16%;">
  <p align="right" style="margin:0in 0in .0001pt;text-align:right;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">3,025,620 shares</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="1%" valign="bottom" style="border:none;padding:0in 0in 0in 0in;width:1.32%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">$</font></p>
  </td>
  <td width="14%" valign="bottom" style="border:none;border-top:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:14.98%;">
  <p align="right" style="margin:0in 0in .0001pt;text-align:right;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">20.06</font></p>
  </td>
  <td width="3%" valign="bottom" style="padding:0in 0in 0in 0in;width:3.04%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(2)</font></p>
  </td>
  <td width="1%" valign="bottom" style="border:none;padding:0in 0in 0in 0in;width:1.32%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">$</font></p>
  </td>
  <td width="16%" valign="bottom" style="border:none;border-top:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:16.02%;">
  <p align="right" style="margin:0in 0in .0001pt;text-align:right;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">60,693,937.20</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="1%" valign="bottom" style="border:none;padding:0in 0in 0in 0in;width:1.32%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">$</font></p>
  </td>
  <td width="16%" valign="bottom" style="border:none;border-top:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:16.02%;">
  <p align="right" style="margin:0in 0in .0001pt;text-align:right;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">7,144.00</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.0%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr height="0">
  <td width="164" style="border:none;"></td>
  <td width="15" style="border:none;"></td>
  <td width="121" style="border:none;"></td>
  <td width="15" style="border:none;"></td>
  <td width="10" style="border:none;"></td>
  <td width="112" style="border:none;"></td>
  <td width="23" style="border:none;"></td>
  <td width="10" style="border:none;"></td>
  <td width="120" style="border:none;"></td>
  <td width="15" style="border:none;"></td>
  <td width="10" style="border:none;"></td>
  <td width="120" style="border:none;"></td>
  <td width="15" style="border:none;"></td>
 </tr>
</table>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="1" width="25%" noshade color="black" align="left">

</font></div>

<p align="left" style="margin:0in 0in .0001pt .25in;text-align:left;text-indent:-.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(1)&#160; Pursuant to Rule 416 under the Securities Act
of 1933, as amended, this Registration Statement shall also cover any
additional shares of common stock which become issuable under the above-named
plans by reason of any stock dividend, stock split, recapitalization or any
other similar transaction effected without the receipt of consideration which
results in an increase in the number of our outstanding shares of common stock.</font></p>

<p align="left" style="margin:0in 0in .0001pt .25in;text-align:left;text-indent:-.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="font-size:10.0pt;margin:0in 0in .0001pt .25in;text-align:left;text-indent:-.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(2)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Estimated pursuant to
Rule 457(h) solely for purposes of calculating the aggregate offering price and
the amount of the registration fee based upon the average of the high and low
prices reported for the shares on The Nasdaq National Market on February&nbsp;3,
2005.</p>

<div style="border:none;border-bottom:double windowtext 9.0pt;padding:0in 0in 0in 0in;">

<p style="border:none;margin:0in 0in .0001pt;padding:0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

</div>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">PART I</font></b></h1>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">INFORMATION REQUIRED IN THE SECTION&nbsp;10(a)
PROSPECTUS</font></b></h1>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h1>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 1.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Plan
Information.*</h2>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 2.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Registrant
Information and Employee Plan Annual Information.*</h2>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="1" width="25%" noshade color="black" align="left">

</font></div>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">*&#160; The documents
containing the information specified in Part I will be delivered in accordance
with Rule 428(b)(1) under the Securities Act of 1933, as amended (the &#147;Securities
Act&#148;).&#160; Such documents are not required
to be, and are not, filed with the Securities and Exchange Commission (the &#147;Commission&#148;),
either as part of this Registration Statement or as prospectuses or prospectus
supplements pursuant to Rule 424 under the Securities Act.&#160; These documents, and the documents
incorporated by reference in this Registration Statement pursuant to Item 3 of
Part II of this Form S-8, taken together, constitute a prospectus that meets
the requirements of Section&nbsp;10(a) of the Securities Act.</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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<div style="font-family:Times New Roman;">

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">PART II</font></b></h1>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h1>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">INFORMATION REQUIRED IN THE REGISTRATION STATEMENT</font></b></h1>

<h1 style="line-height:normal;margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h1>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 3.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Incorporation
of Documents by Reference.</h2>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">The following documents,
which have been filed by optionsXpress Holdings, Inc. (the &#147;Company&#148;) with the
Commission, are incorporated in this Registration Statement by reference:</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(a)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>The Company&#146;s
Prospectus, dated January&nbsp;26, 2005, filed pursuant to Rule 424(b) of the
Securities Act, which relates to the Company&#146;s Registration Statement on Form
S-1 (Registration No. 333-119967) (as amended and including exhibits, the &#147;S-1
Registration Statement&#148;).</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(b)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>The
description of the Company&#146;s common stock, par value $0.0001 per share,
included under the caption &#147;Description of Capital Stock&#148; in the Prospectus
forming a part of the S-1 Registration Statement, which description has been
incorporated by reference in Item&nbsp;1 of the Company&#146;s Registration
Statement on Form&nbsp;8-A, filed pursuant to Section&nbsp;12 of the Securities
Exchange Act of 1934, as amended (the &#147;Exchange Act&#148;), on January&nbsp;27,
2005.</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">All documents
subsequently filed by the Company pursuant to Sections 13(a), 13(c), 14 and
15(d) of the Exchange Act, prior to the filing of a post-effective amendment
which indicates that all securities offered hereby have been sold or which
deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference herein and to be a part hereof from the date of
filing of such documents.</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Any statement contained
in a document incorporated or deemed to be incorporated by reference herein
shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a statement contained herein or in any other
subsequently filed document which also is or is deemed to be incorporated by
reference herein modifies or supersedes such statement.&#160; Any statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of
this Registration Statement.</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 4.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Description
of Securities.&#160; </h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Not
applicable.</font></p>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 5.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Interests
of Named Experts and Counsel.&#160; </h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="margin:0in 0in .0001pt;text-indent:1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">Not applicable.</font></b></h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 6.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Indemnification
of Directors and Officers.</h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">The Company is
incorporated under the laws of the State of Delaware.&#160; Its Amended and Restated Certificate of
Incorporation provides, as authorized by Section&nbsp;102(b)(7) of the Delaware
General Company Law (the &#147;DGCL&#148;), that a director of the Company will not be
personally liable to the Company or its stockholders for monetary damages for
breach of fiduciary duty as a director, except for liability:</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(a)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>for
any transaction from which the director derives an improper personal benefit;</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(b)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>for
any act or omission not in good faith or that involves intentional misconduct
or a knowing violation of law;</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(c)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>for
any improper payment of dividends or redemption of shares; or</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(d)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>for
any breach of the director&#146;s duty of loyalty to the Company or its
stockholders.</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">The Company&#146;s Amended and
Restated Certificate of Incorporation further provides, as permitted by Section&nbsp;145
of the DGCL, that each person who was or is a party or is threatened to be made
a party to or is otherwise involved with any action, suit or proceeding,
whether civil, criminal, administrative or investigative, by reason of the fact
that he or she is or was a director or officer of the Company or is or was
serving at the request of</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">II-1</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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<div style="font-family:Times New Roman;">

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">the Company as a
director or officer of another company or other enterprise (an &#147;indemnitee&#148;),&#160; will be indemnified and held harmless by the
Company to the fullest extent authorized by the DGCL, against all expense,
liability and loss (including attorneys&#146; fees and related disbursements,
judgments, fines, excise taxes or penalties under the Employee Retirement
Income Security Act of 1974, as amended) actually and reasonably incurred or
suffered by such indemnitee in connection therewith.&#160; This right of indemnification includes the
obligation of the Company to provide an advance of expenses, although the
indemnitee shall be required to repay such an advance if there is a judicial
determination that the indemnitee was not entitled to the indemnification.</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 7.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Exemption
from Registration Claimed.&#160; </h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Not
applicable.</font></p>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 8.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Exhibits.&#160; </h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="margin:0in 0in .0001pt 1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">Reference
is made to the attached Exhibit Index, which is incorporated by reference
herein.</font></b></h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h2 style="font-size:10.0pt;margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;">Item 9.</font></b><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Undertakings.</h2>

<h2 style="margin:0in 0in .0001pt 1.0in;text-indent:-1.0in;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:normal;">&nbsp;</font></b></h2>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(a)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>The
undersigned registrant hereby undertakes:</h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(1) To file, during any period in which offers or
sales are being made, a post-effective amendment to the Registration Statement:</font></h5>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h5>

<h4 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(i)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>To
include any prospectus required by Section&nbsp;10(a)(3) of the Securities Act;</h4>

<h4 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h4>

<h4 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(ii)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>To
reflect in the prospectus any facts or events arising after the effective date
of the Registration Statement (or most recent post-effective amendment thereof)
which, individually or in the aggregate, represent a fundamental change in the
information set forth in the registration statement.&#160; Notwithstanding the foregoing, any increase
or decrease in volume of securities offered (if the total dollar value of
securities offered would not exceed that which was registered) and any
deviation from the low or high end of the estimated maximum offering range may
be reflected in the form of prospectus filed with the Commission pursuant to
Rule 424(b) if, in the aggregate, the changes in volume and price represent no
more than a 20% change in the maximum aggregate offering price set forth in the
&#147;Calculation of Registration Fee&#148; table in the effective registration
statement; and</h4>

<h4 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h4>

<h4 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(iii)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>To include any material
information with respect to the plan of distribution not previously disclosed
in the Registration Statement or any material change to such information in the
Registration Statement;</h4>

<h4 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h4>

<p style="font-size:10.0pt;margin:0in 0in .0001pt;"><u><font size="2" face="Times New Roman" style="font-size:10.0pt;">provided</font></u>, <u>however</u>, that
paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if the information required to
be included in a post-effective amendment by those paragraphs is contained in
periodic reports filed with or furnished to the Commission by the registrant
pursuant to Section&nbsp;13 or Section&nbsp;15(d) of the Exchange Act that are
incorporated by reference in the Registration Statement.</p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(2) That, for the purpose of determining any liability
under the Securities Act, each such post-effective amendment shall be deemed to
be a new registration statement relating to the securities offered therein, and
the offering of such securities at that time shall be deemed to be the initial
bona fide offering thereof; and</font></h5>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h5>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(3) To remove from registration by means of a
post-effective amendment any of the securities being registered which remain
unsold at the termination of the offering.</font></h5>

<h5 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.5in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h5>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(b)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>The
undersigned registrant hereby undertakes that, for purposes of determining any
liability under the Securities Act, each filing of the Company&#146;s annual report
pursuant to Section&nbsp;13(a) or Section&nbsp;15(d) of the Exchange Act (and,
where applicable, each filing of an employee benefit plan&#146;s annual report
pursuant to Section&nbsp;15(d) of the Exchange Act) that is incorporated by</h3>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">II-2</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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<div style="font-family:Times New Roman;">

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">reference in the Registration Statement shall be deemed to be a new
registration statement relating to the securities offered herein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.</font></h3>

<h3 align="left" style="font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></h3>

<h3 align="left" style="font-size:10.0pt;font-weight:normal;margin:0in 0in .0001pt 1.0in;text-align:left;text-indent:.25in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">(c)</font><font size="1" style="font-size:3.0pt;">&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160;&#160; </font>Insofar
as indemnification for liabilities arising under the Securities Act may be
permitted to directors, officers and controlling persons of the registrant
pursuant to the foregoing provisions, or otherwise, the registrant has been
advised that in the opinion of the Commission such indemnification is against
public policy as expressed in the Securities Act and is, therefore,
unenforceable.&#160; In the event that a claim
for indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling
precedent, submit to a court of appropriate jurisdiction the question whether
such indemnification by it is against public policy as expressed in the
Securities Act and will be governed by the final adjudication of such issue.</h3>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">II-3</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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<div>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-decoration:underline;text-transform:uppercase;"><b><u><font size="2" face="Times New Roman" style="font-size:10.0pt;text-transform:none;">SIGNATURES</font></u></b></p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Pursuant to the
requirements of the Securities Act of 1933, the registrant certifies that it
has reasonable grounds to believe that it meets all of the requirements for
filing on Form S-8 and has duly caused this Registration Statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the City of
Chicago, State of Illinois, on February&nbsp;9, 2005.</font></p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<table border="0" cellspacing="0" cellpadding="0" width="100%" style="border-collapse:collapse;width:100.0%;">
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="38%" colspan="2" valign="top" style="padding:0in 0in 0in 0in;width:38.34%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">optionsXpress
  Holdings, Inc.</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="34%" valign="top" style="padding:0in 0in 0in 0in;width:34.34%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.0%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="34%" valign="top" style="padding:0in 0in 0in 0in;width:34.34%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.0%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">By:</font></p>
  </td>
  <td width="34%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:34.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ David A.
  Fisher</font></p>
  </td>
 </tr>
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="38%" colspan="2" valign="top" style="padding:0in 0in 0in 0in;width:38.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Name: David A.
  Fisher</font></p>
  </td>
 </tr>
 <tr>
  <td width="61%" valign="top" style="padding:0in 0in 0in 0in;width:61.66%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="38%" colspan="2" valign="top" style="padding:0in 0in 0in 0in;width:38.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Title: Chief
  Financial Officer</font></p>
  </td>
 </tr>
</table>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">POWER OF ATTORNEY</font></b></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">KNOW ALL MEN BY THESE
PRESENTS, that each person whose signature appears below constitutes and
appoints David S. Kalt and David A. Fisher and each of them his or her true and
lawful attorney-in-fact and agent, with full power of substitution and
resubstitution, for him or her and in his or her name, place and stead, in any
and all capacities (including his or her capacity as a director and/or officer)
to sign any or all amendments (including post-effective amendments) to this
registration statement, and to file the same, with all exhibits thereto, and
other documents in connection therewith, with the Securities and Exchange
Commission, granting unto said attorney-in-fact and agent full power and
authority to do and perform each and every act and thing requisite and
necessary to be done in and about the premises, as fully to all intents and
purposes as he or she might or could do in person, hereby ratifying and
confirming all that said attorney-in-fact and agent or his substitute or
substitutes, may lawfully do or cause to be done by virtue hereof.</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Pursuant to the
requirements of the Securities Act of 1933, this Registration Statement has
been signed by the following persons in the capacities indicated on February&nbsp;9,
2005.</font></p>

<p align="left" style="margin:0in 0in .0001pt;text-align:left;text-indent:1.0in;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<table border="0" cellspacing="0" cellpadding="0" width="80%" style="border-collapse:collapse;margin-left:1.0in;width:80.0%;">
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Signature</font></b></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="48%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:48.92%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Title</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ James A. Gray</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Chairman of the
  Board</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">James A. Gray</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ David S. Kalt</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Chief Executive
  Officer (Principal Executive</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">David S. Kalt</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Officer) and
  Director</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ Ned W. Bennett</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Chief Operating
  Officer and Director</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Ned W. Bennett</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ David A. Fisher</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Chief Financial
  Officer (Principal Financial and</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">David A. Fisher</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Accounting
  Officer)</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">/s/ Christopher J. Dean</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Director</font></p>
  </td>
 </tr>
 <tr>
  <td width="46%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:46.14%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Christopher J. Dean</font></p>
  </td>
  <td width="4%" valign="top" style="padding:0in 0in 0in 0in;width:4.94%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="48%" valign="top" style="padding:0in 0in 0in 0in;width:48.92%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
 </tr>
</table>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">II-4</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
<!-- SEQ.=1,FOLIO='II-4',FILE='C:\JMS\sshanka\05-2846-1\task296789\2846-1-ba.htm',USER='kranganathan',CD='Feb  9 05:19 2005' -->


<br clear="all" style="page-break-before:always;">


<div>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<p style="font-weight:bold;margin:0in 0in .0001pt;text-align:center;text-decoration:underline;text-transform:uppercase;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;text-decoration:none;text-transform:none;">EXHIBIT INDEX</font></b></p>

<p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<table border="0" cellspacing="0" cellpadding="0" width="100%" style="border-collapse:collapse;width:100.0%;">
 <tr>
  <td width="7%" valign="top" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Exhibit<br>
  Number</font></b></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:1.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="90%" valign="bottom" style="border:none;border-bottom:solid windowtext 1.0pt;padding:0in 0in 0in 0in;width:90.4%;">
  <p align="center" style="margin:0in 0in .0001pt;text-align:center;"><b><font size="1" face="Times New Roman" style="font-size:8.0pt;font-weight:bold;">Description</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
  <td width="90%" valign="top" style="border:none;padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><b><font size="2" face="Times New Roman" style="font-size:10.0pt;font-weight:bold;">&nbsp;</font></b></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">4.1</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Form of
  certificate of common stock of optionsXpress Holdings, Inc., incorporated by
  reference to Exhibit 4.1 of the Company&#146;s S-1 Registration Statement.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">4.2</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">2001 Equity
  Incentive Plan, incorporated by reference to Exhibit 10.9 of the Company&#146;s
  S-1 Registration Statement.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">4.3</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">2005 Equity
  Incentive Plan, incorporated by reference to Exhibit 10.10 of the Company&#146;s
  S-1 Registration Statement.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">4.4</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">2005 Employee
  Stock Purchase Plan, incorporated by reference to Exhibit 10.11 of the
  Company&#146;s S-1 Registration Statement.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">4.5</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Form of Stock
  Option Award Agreement.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">5.1</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Opinion of
  Kirkland &amp; Ellis LLP.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">23.1</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Consent of Ernst
  &amp; Young LLP.</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">23.2</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Consent of
  Kirkland &amp; Ellis LLP (included in Exhibit 5.1).</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>
  </td>
 </tr>
 <tr>
  <td width="7%" valign="top" style="padding:0in 0in 0in 0in;width:7.26%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">24.1</font></p>
  </td>
  <td width="2%" valign="bottom" style="padding:0in 0in 0in 0in;width:2.34%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:1.0pt;">&nbsp;</font></p>
  </td>
  <td width="90%" valign="top" style="padding:0in 0in 0in 0in;width:90.4%;">
  <p style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">Powers of
  Attorney (included in Part II).</font></p>
  </td>
 </tr>
</table>

<p align="center" style="margin:0in 0in .0001pt;text-align:center;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">&nbsp;</font></p>

<div style="margin:0in 0in .0001pt;"><font size="2" face="Times New Roman" style="font-size:10.0pt;">

<hr size="2" width="100%" noshade color="gray" align="left">

</font></div>

</div>
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{"company-data": {"conformed-name": "optionsXpress Holdings, Inc.", "cik": "0001299688", "assigned-sic": "6211", "irs-number": "000000000", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-122664", "film-number": "05589324"}, "business-address": {"street1": "39 SOUTH LASALLE STREET", "street2": "SUITE 220", "city": "CHICAGO", "state": "IL", "zip": "60603", "phone": "312-630-3300"}, "mail-address": {"street1": "39 SOUTH LASALLE STREET", "street2": "SUITE 220", "city": "CHICAGO", "state": "IL", "zip": "60603"}}
As filed with the
Securities and Exchange Commission on February 9, 2005
Registration
No. 333-
UNITED
STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 
20549
FORM S-8
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933
OPTIONSXPRESS HOLDINGS, INC.
(Exact name of registrant as
specified in its charter)
Delaware
20-1444525
(State or other jurisdiction of
incorporation or organization)
(I.R.S. Employer
Identification No.)
39 South LaSalle Street, Suite 220
Chicago, Illinois 60603
60603
(Address of Principal Executive Offices)
(Zip Code)
2001 Equity Incentive Plan
2005 Equity Incentive Plan
2005 Employee Stock Purchase Plan
(Full titles of the plans)
David S. Kalt, Chief Executive Officer
optionsXpress Holdings, Inc.
39 South LaSalle Street, Suite 220
Chicago, Illinois 60603
(Name and address of
agent for service)
(312) 630-3300
(Telephone number, including area code, of agent for service)
Copy to
:
Sanford E. Perl, P.C.
Gerald T. Nowak
Kirkland & Ellis LLP
200 E. Randolph Drive
Chicago, Illinois 60601
Telephone: (312) 861-2000
Telecopy: (312) 861-2200
CALCULATION OF REGISTRATION FEE
Title of securities to be
registered
Amount to be
registered (1)
Proposed maximum
offering price per
share
Proposed maximum
aggregate offering
price
Amount of
registration
fee
Common Stock, par value $0.0001 per share
3,025,620 shares
$
20.06
(2)
$
60,693,937.20
$
7,144.00
(1)  Pursuant to Rule 416 under the Securities Act
of 1933, as amended, this Registration Statement shall also cover any
additional shares of common stock which become issuable under the above-named
plans by reason of any stock dividend, stock split, recapitalization or any
other similar transaction effected without the receipt of consideration which
results in an increase in the number of our outstanding shares of common stock.
(2)
Estimated pursuant to
Rule 457(h) solely for purposes of calculating the aggregate offering price and
the amount of the registration fee based upon the average of the high and low
prices reported for the shares on The Nasdaq National Market on February 3,
2005.
PART I
INFORMATION REQUIRED IN THE SECTION 10(a)
PROSPECTUS
Item 1.
Plan
Information.*
Item 2.
Registrant
Information and Employee Plan Annual Information.*
*  The documents
containing the information specified in Part I will be delivered in accordance
with Rule 428(b)(1) under the Securities Act of 1933, as amended (the "Securities
Act").  Such documents are not required
to be, and are not, filed with the Securities and Exchange Commission (the "Commission"),
either as part of this Registration Statement or as prospectuses or prospectus
supplements pursuant to Rule 424 under the Securities Act.  These documents, and the documents
incorporated by reference in this Registration Statement pursuant to Item 3 of
Part II of this Form S-8, taken together, constitute a prospectus that meets
the requirements of Section 10(a) of the Securities Act.
PART II
INFORMATION REQUIRED IN THE REGISTRATION STATEMENT
Item 3.
Incorporation
of Documents by Reference.
The following documents,
which have been filed by optionsXpress Holdings, Inc. (the "Company") with the
Commission, are incorporated in this Registration Statement by reference:
(a)
The Company's
Prospectus, dated January 26, 2005, filed pursuant to Rule 424(b) of the
Securities Act, which relates to the Company's Registration Statement on Form
S-1 (Registration No. 333-119967) (as amended and including exhibits, the "S-1
Registration Statement").
(b)
The
description of the Company's common stock, par value $0.0001 per share,
included under the caption "Description of Capital Stock" in the Prospectus
forming a part of the S-1 Registration Statement, which description has been
incorporated by reference in Item 1 of the Company's Registration
Statement on Form 8-A, filed pursuant to Section 12 of the Securities
Exchange Act of 1934, as amended (the "Exchange Act"), on January 27,
2005.
All documents
subsequently filed by the Company pursuant to Sections 13(a), 13(c), 14 and
15(d) of the Exchange Act, prior to the filing of a post-effective amendment
which indicates that all securities offered hereby have been sold or which
deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference herein and to be a part hereof from the date of
filing of such documents.
Any statement contained
in a document incorporated or deemed to be incorporated by reference herein
shall be deemed to be modified or superseded for purposes of this Registration
Statement to the extent that a statement contained herein or in any other
subsequently filed document which also is or is deemed to be incorporated by
reference herein modifies or supersedes such statement.  Any statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of
this Registration Statement.
Item 4.
Description
of Securities.
Not
applicable.
Item 5.
Interests
of Named Experts and Counsel.
Not applicable.
Item 6.
Indemnification
of Directors and Officers.
The Company is
incorporated under the laws of the State of Delaware.  Its Amended and Restated Certificate of
Incorporation provides, as authorized by Section 102(b)(7) of the Delaware
General Company Law (the "DGCL"), that a director of the Company will not be
personally liable to the Company or its stockholders for monetary damages for
breach of fiduciary duty as a director, except for liability:
(a)
for
any transaction from which the director derives an improper personal benefit;
(b)
for
any act or omission not in good faith or that involves intentional misconduct
or a knowing violation of law;
(c)
for
any improper payment of dividends or redemption of shares; or
(d)
for
any breach of the director's duty of loyalty to the Company or its
stockholders.
The Company's Amended and
Restated Certificate of Incorporation further provides, as permitted by Section 145
of the DGCL, that each person who was or is a party or is threatened to be made
a party to or is otherwise involved with any action, suit or proceeding,
whether civil, criminal, administrative or investigative, by reason of the fact
that he or she is or was a director or officer of the Company or is or was
serving at the request of
II-1
the Company as a
director or officer of another company or other enterprise (an "indemnitee"),  will be indemnified and held harmless by the
Company to the fullest extent authorized by the DGCL, against all expense,
liability and loss (including attorneys' fees and related disbursements,
judgments, fines, excise taxes or penalties under the Employee Retirement
Income Security Act of 1974, as amended) actually and reasonably incurred or
suffered by such indemnitee in connection therewith.  This right of indemnification includes the
obligation of the Company to provide an advance of expenses, although the
indemnitee shall be required to repay such an advance if there is a judicial
determination that the indemnitee was not entitled to the indemnification.
Item 7.
Exemption
from Registration Claimed.
Not
applicable.
Item 8.
Exhibits.
Reference
is made to the attached Exhibit Index, which is incorporated by reference
herein.
Item 9.
Undertakings.
(a)
The
undersigned registrant hereby undertakes:
(1) To file, during any period in which offers or
sales are being made, a post-effective amendment to the Registration Statement:
(i)
To
include any prospectus required by Section 10(a)(3) of the Securities Act;
(ii)
To
reflect in the prospectus any facts or events arising after the effective date
of the Registration Statement (or most recent post-effective amendment thereof)
which, individually or in the aggregate, represent a fundamental change in the
information set forth in the registration statement.  Notwithstanding the foregoing, any increase
or decrease in volume of securities offered (if the total dollar value of
securities offered would not exceed that which was registered) and any
deviation from the low or high end of the estimated maximum offering range may
be reflected in the form of prospectus filed with the Commission pursuant to
Rule 424(b) if, in the aggregate, the changes in volume and price represent no
more than a 20% change in the maximum aggregate offering price set forth in the
"Calculation of Registration Fee" table in the effective registration
statement; and
(iii)
To include any material
information with respect to the plan of distribution not previously disclosed
in the Registration Statement or any material change to such information in the
Registration Statement;
provided
,
however
, that
paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if the information required to
be included in a post-effective amendment by those paragraphs is contained in
periodic reports filed with or furnished to the Commission by the registrant
pursuant to Section 13 or Section 15(d) of the Exchange Act that are
incorporated by reference in the Registration Statement.
(2) That, for the purpose of determining any liability
under the Securities Act, each such post-effective amendment shall be deemed to
be a new registration statement relating to the securities offered therein, and
the offering of such securities at that time shall be deemed to be the initial
bona fide offering thereof; and
(3) To remove from registration by means of a
post-effective amendment any of the securities being registered which remain
unsold at the termination of the offering.
(b)
The
undersigned registrant hereby undertakes that, for purposes of determining any
liability under the Securities Act, each filing of the Company's annual report
pursuant to Section 13(a) or Section 15(d) of the Exchange Act (and,
where applicable, each filing of an employee benefit plan's annual report
pursuant to Section 15(d) of the Exchange Act) that is incorporated by
II-2
reference in the Registration Statement shall be deemed to be a new
registration statement relating to the securities offered herein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.
(c)
Insofar
as indemnification for liabilities arising under the Securities Act may be
permitted to directors, officers and controlling persons of the registrant
pursuant to the foregoing provisions, or otherwise, the registrant has been
advised that in the opinion of the Commission such indemnification is against
public policy as expressed in the Securities Act and is, therefore,
unenforceable.  In the event that a claim
for indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling
precedent, submit to a court of appropriate jurisdiction the question whether
such indemnification by it is against public policy as expressed in the
Securities Act and will be governed by the final adjudication of such issue.
II-3
SIGNATURES
Pursuant to the
requirements of the Securities Act of 1933, the registrant certifies that it
has reasonable grounds to believe that it meets all of the requirements for
filing on Form S-8 and has duly caused this Registration Statement to be signed
on its behalf by the undersigned, thereunto duly authorized, in the City of
Chicago, State of Illinois, on February 9, 2005.
optionsXpress
  Holdings, Inc.
By:
/s/ David A.
  Fisher
Name: David A.
  Fisher
Title: Chief
  Financial Officer
POWER OF ATTORNEY
KNOW ALL MEN BY THESE
PRESENTS, that each person whose signature appears below constitutes and
appoints David S. Kalt and David A. Fisher and each of them his or her true and
lawful attorney-in-fact and agent, with full power of substitution and
resubstitution, for him or her and in his or her name, place and stead, in any
and all capacities (including his or her capacity as a director and/or officer)
to sign any or all amendments (including post-effective amendments) to this
registration statement, and to file the same, with all exhibits thereto, and
other documents in connection therewith, with the Securities and Exchange
Commission, granting unto said attorney-in-fact and agent full power and
authority to do and perform each and every act and thing requisite and
necessary to be done in and about the premises, as fully to all intents and
purposes as he or she might or could do in person, hereby ratifying and
confirming all that said attorney-in-fact and agent or his substitute or
substitutes, may lawfully do or cause to be done by virtue hereof.
Pursuant to the
requirements of the Securities Act of 1933, this Registration Statement has
been signed by the following persons in the capacities indicated on February 9,
2005.
Signature
Title
/s/ James A. Gray
Chairman of the
  Board
James A. Gray
/s/ David S. Kalt
Chief Executive
  Officer (Principal Executive
David S. Kalt
Officer) and
  Director
/s/ Ned W. Bennett
Chief Operating
  Officer and Director
Ned W. Bennett
/s/ David A. Fisher
Chief Financial
  Officer (Principal Financial and
David A. Fisher
Accounting
  Officer)
/s/ Christopher J. Dean
Director
Christopher J. Dean
II-4
EXHIBIT INDEX
Exhibit
Number
Description
4.1
Form of
  certificate of common stock of optionsXpress Holdings, Inc., incorporated by
  reference to Exhibit 4.1 of the Company's S-1 Registration Statement.
4.2
2001 Equity
  Incentive Plan, incorporated by reference to Exhibit 10.9 of the Company's
  S-1 Registration Statement.
4.3
2005 Equity
  Incentive Plan, incorporated by reference to Exhibit 10.10 of the Company's
  S-1 Registration Statement.
4.4
2005 Employee
  Stock Purchase Plan, incorporated by reference to Exhibit 10.11 of the
  Company's S-1 Registration Statement.
4.5
Form of Stock
  Option Award Agreement.
5.1
Opinion of
  Kirkland & Ellis LLP.
23.1
Consent of Ernst
  & Young LLP.
23.2
Consent of
  Kirkland & Ellis LLP (included in Exhibit 5.1).
24.1
Powers of
  Attorney (included in Part II).