<PAGE>

     As filed with the Securities and Exchange Commission on April 28, 2000
                                                           Registration No. 333-
================================================================================


                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549
                             ----------------------


                                    FORM S-8
                             REGISTRATION STATEMENT
                                     Under
                           The Securities Act of 1933

                                WEB STREET, INC.
             (Exact Name of Registrant as Specified in its Charter)

                 Delaware                          36-4212401
      (State or Other Jurisdiction             (I.R.S. Employer
     of Incorporation or Organization)          Identification No.)

                 510 Lake Cook Road, Deerfield, Illinois 60015
        (Address of Principal Executive Offices)      (Zip Code)

               Web Street Financial Group, Inc. Stock Option Plan
                   Web Street, Inc. 1999 Stock Incentive Plan
                Option Agreements Listed on Attached Schedule I
               Web Street, Inc. 1999 Employee Stock Purchase Plan
                           (Full Title of the Plans)

                              Stuart A. Cohn, Esq.
                  Executive Vice President and General Counsel
                 510 Lake Cook Road, Deerfield, Illinois 60015
                    (Name and Address of Agent for Service)
                                 (847) 444-4700
         (Telephone Number, Including Area Code, of Agent for Service)

                                   Copies to:
                               Mark D. Wood, Esq.
                              Adam R. Klein, Esq.
                              Katten Muchin Zavis
                       525 West Monroe Street, Suite 1600
                         Chicago, Illinois  60661-3693
                                 (312) 902-5200
                           ---------------------------


                        CALCULATION OF REGISTRATION FEE
<TABLE>
<CAPTION>
====================================================================================================================
                                                           Proposed Maximum     Proposed Maximum
                                          Amount To Be      Offering Price    Aggregate Offering       Amount Of
Title Of Securities To Be Registered     Registered (1)        Per Share             Price          Registration Fee
--------------------------------------------------------------------------------------------------------------------
<S>                                     <C>                <C>                <C>                   <C>
Common Stock, $0.01 par value
 (Stock Option Plan)..................  1,298,000 shares         $6.47(2)          $ 8,398,060(2)           $2,335
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (1999 Stock Incentive Plan)..........  4,000,000 shares         $8.19(3)          $17,216,671(3)           $4,786
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (Option Agreements)..................    569,377 shares         $ .06(4)          $    34,163(4)           $   10
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (1999 Stock Purchase Plan)...........  1,000,000 shares         $3.85(5)          $ 3,850,000(5)           $1,070
--------------------------------------------------------------------------------------------------------------------
         Total........................  6,867,377 shares            --                      --              $8,201
====================================================================================================================
</TABLE>
(1) This registration statement also covers an indeterminate number of shares of
    Web Street, Inc. Common Stock that may be issuable by reason of stock
    splits, stock dividends or similar transactions in accordance with Rule 416
    under the Securities Act of 1933.

(2) Based upon the weighted average exercise price for the currently outstanding
    options granted under this plan. These amounts are used solely for the
    purpose of calculating the registration fee pursuant to Rule 457(h)(1) under
    the Securities Act.

(3) Based upon (i) the weighted average exercise price of $8.19 per share for
    currently outstanding options to purchase 418,588 shares of Common Stock
    granted under this plan and (ii) the average of the high and low sales
    prices of the Common Stock as reported on the Nasdaq National Market on
    April 26, 2000, which was $3.85, with respect to 3,581,412 shares of Common
    Stock which may be granted under this plan. These amounts are used solely
    for the purpose of calculating the registration fee pursuant to Rules
    457(h)(1) and 457(c) under the Securities Act.

(4) Based upon the weighted average exercise price for the currently outstanding
    options granted under these agreements. These amounts are used solely for
    the purpose of calculating the registration fee pursuant to Rule 457(h)(1)
    under the Securities Act.

(5) Based on the average of the high and low sales prices of the Common Stock as
    reported on the Nasdaq National Market on April 26, 2000. These amounts
    are used solely for the purpose of calculating the registration fee pursuant
    to Rule 457(c) under the Securities Act.
================================================================================
<PAGE>

                                   SCHEDULE I
                                   ----------


     Option Agreements between Web Street Financial Group, Inc. and the
     following employees and consultants:

     Fred Allen
     Manuel Calderon
     Ryan Carpel
     Stuart Cohn
     Barbara Escobar
     Paul Gakhal
     Michael Graf
     Michael Grimes
     Jason Hersh
     Vanesa Horton
     Gary Just
     William Mania
     Christopher Mazzacono
     Melvin Pinkham
     D. Jonathan Rosenberg
     Jonah Rosenberg
     Robert Rosenberg
     Jeffrey Schulhof
     Alan Seleman
     Jeffrey Williams
     Tom Wilson
     Saul Zadik
     Steve Zakrzewski


                                     I-1
<PAGE>


                                    PART I
             INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS

     The information called for in Part I of Form S-8 is currently included in
the prospectuses for the Web Street Financial Group, Inc. Stock Option Plan, the
Web Street, Inc. 1999 Stock Incentive Plan, the option agreements listed on the
attached Schedule I and the Web Street, Inc. 1999 Employee Stock Purchase Plan
(collectively, the "Plans"), and is not being filed with, or included in, this
Form S-8 in accordance with the rules and regulations of the SEC. Web Street
will not issue any additional options under the Web Street Financial Group, Inc.
Stock Option Plan or the option agreements listed on the attached Schedule I.
Web Street Financial Group, Inc. is the former name of Web Street, Inc.



                                      I-2
<PAGE>


                                    PART II
              INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3.  Incorporation of Documents by Reference.

     The following documents filed by the Registrant with the SEC are
incorporated by reference in this registration statement:

     (a)  The Registrant's Annual Report on Form 10-K for the fiscal year ended
          December 31, 1999; and

     (b)  The description of the Registrant's common stock in the Registrant's
          Registration Statement on Form 8-A filed on October 18, 1999 pursuant
          to the Securities Exchange Act of 1934, and all subsequent amendments
          and reports filed for the purpose of updating the description.

     In addition, all documents that the Registrant files pursuant to Sections
13(a), 13(c), 14 or 15(d) of the Exchange Act after the date of this
registration statement and before the filing of a post-effective amendment
indicating that all securities offered pursuant to this registration statement
have been sold or deregistering all the securities then remaining unsold shall
be deemed to be incorporated by reference in this registration statement and to
be part of this registration statement from the date of filing of those
documents. Any statement contained in a document incorporated or deemed to be
incorporated by reference in this registration statement shall be deemed to be
modified or superseded for purposes of this registration statement to the extent
that a statement contained in this registration statement or in any subsequently
filed document which also is or is deemed to be incorporated by reference in
this registration statement modifies or supersedes that statement.

     The Registrant will provide without charge to each person who has received
a copy of any prospectus to which this registration statement relates, upon the
written or oral request of that person, a copy of any or all the documents that
have been or may be incorporated by reference into this registration statement,
other than exhibits to those documents, unless the exhibits are incorporated by
reference in those documents. Written requests for copies should be directed to
the Registrant's principal executive offices at 510 Lake Cook Road, Deerfield,
Illinois 60015, Attention: Corporate Secretary. Telephone requests for copies
should be directed to the Registrant's Corporate Secretary at (847) 444-4700.

Item 4. Description of Securities.

     Not applicable.

Item 5. Interests of Named Experts and Counsel.

     Not applicable.

Item 6. Indemnification of Directors and Officers.

     As permitted by the Delaware General Corporation Law, the Registrant's
Amended and Restated Certificate of Incorporation contains provisions that
eliminate the personal liability of the Registrant's directors to the Registrant
or its stockholders for monetary damages for the breach or alleged breach of
their fiduciary duty as a director, except for liability for:

                                     II-1
<PAGE>


     .    any breach of their duty of loyalty to the Registrant or its
          stockholders;

     .    acts or omissions not in good faith or which involve intentional
          misconduct or a knowing violation of law;

     .    willful or negligent conduct in paying dividends or repurchasing stock
          out of other than lawfully available funds; and

     .    any transaction from which the director derived an improper personal
          benefit.

     The Registrant's Amended and Restated Certificate of Incorporation also
contains provisions that require the Registrant to indemnify its directors and
permit the Registrant to indemnify its officers and employees to the fullest
extent permitted by Delaware corporate law. However, the Registrant is not
obligated to indemnify a person:

     .    with respect to proceedings, claims or actions initiated or brought
          voluntarily by the person and not by way of defense; and

     .    for any amounts paid in settlement of an action indemnified against by
          the Registrant without its prior written consent.

The Registrant has entered into indemnity agreements with each of its directors
and executive officers providing for this indemnification and containing the
Registrant's covenant to maintain directors' and officers' liability insurance.

     Reference is made to Section 145 of the General Corporation Law of the
State of Delaware which provides for indemnification of directors and officers
in certain circumstances.

Item 7. Exemption from Registration Claimed.

     Not applicable.

Item 8. Exhibits.

     4.1  The Registrant's Amended and Restated Certificate of Incorporation,
          incorporated by reference to Exhibit 3.1 to the Registrant's Annual
          Report on Form 10-K for the fiscal year ended December 31, 1999
          (the "1999 10-K").

     4.2  The Registrant's Amended and Restated Bylaws, incorporated by
          reference to Exhibit 3.2 to the 1999 10-K.

     4.3  Specimen stock certificate representing common stock, incorporated by
          reference to Exhibit 4 to the Registrant's Registration Statement on
          Form S-1, as amended (Registration Statement No. 333-85849) (the
          "IPO Registration Statement").

     4.4  Web Street Financial Group, Inc. Stock Option Plan, incorporated by
          reference to Exhibit 10.1 to the IPO Registration Statement.

     4.5  Form of Option Agreement under the Stock Option Plan, incorporated by
          reference to Exhibit 10.2 to the IPO Registration Statement.


                                     II-2
<PAGE>


     4.6  Form of Option Agreement with various employees and consultants prior
          to the Stock Option Plan, incorporated by reference to Exhibit 10.3 to
          the IPO Registration Statement.

     4.7  The Registrant's 1999 Stock Incentive Plan, incorporated by reference
          to Exhibit 10.4 to the IPO Registration Statement.

     4.8  Form of Option Agreement under the 1999 Stock Incentive Plan,
          incorporated by reference to Exhibit 10.5 to the IPO Registration
          Statement.

     4.9  The Registrant's 1999 Employee Stock Purchase Plan.

     5    Opinion of Stuart A. Cohn, General Counsel of the Registrant, as to
          the legality of the shares of common stock being offered under the
          Plans.

    23.1  Consent of Arthur Andersen LLP.

    23.2  Consent of Stuart A. Cohn (contained in his opinion filed as
          Exhibit 5).

    24    Power of Attorney (included on the signature page of this registration
          statement).

                                     II-3
<PAGE>


Item 9. Undertakings.

     1.   The Registrant hereby undertakes:

          (a)  To file, during any period in which offers or sales are being
     made, a post-effective amendment to this 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 the 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; 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)(i) and (a)(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 by the Registrant
     pursuant to Section 13 or Section 15(d) of the Exchange Act that are
     incorporated by reference in the registration statement.

          (b)  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.

          (c)  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.

     2.   The Registrant hereby undertakes that, for the purpose of determining
any liability under the Securities Act, each filing of its 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 reference in the
registration statement 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.

     3.   Insofar as indemnification for liabilities arising under the
Securities Act may be permitted to the Registrant's directors, officers and
controlling persons pursuant to the foregoing provisions or otherwise, the
Registrant has been advised that in the opinion of the SEC 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-4
<PAGE>


                                  SIGNATURES

     Pursuant to the requirements of the Securities Act, 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 Deerfield, State of Illinois, on this 28th day of
April, 2000.

                                     WEB STREET, INC.

                                     By: /S/ JOSEPH J. FOX
                                         ---------------------------------------
                                         Joseph J. Fox
                                         Chief Executive Officer and Co-Chairman
                                         of the Board

                               POWER OF ATTORNEY

     Each person whose signature appears below hereby constitutes and appoints
Joseph J. Fox, Stuart A. Cohn and Mark D. Wood, and each of them, his true and
lawful attorneys-in-fact and agents, with full power of substitution, to sign on
his behalf, individually and in each capacity stated below, all amendments and
post-effective amendments to this registration statement on Form S-8 and to file
the same, with all exhibits thereto and any other documents in connection
therewith, with the SEC under the Securities Act, granting unto said
attorneys-in-fact and agents 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 and to all intents and purposes as each might or could do in
person, hereby ratifying and confirming each act that said attorneys-in-fact and
agents may lawfully do or cause to be done by virtue thereof.

     Pursuant to the requirements of the Securities Act, this registration
statement has been signed by the following persons in the capacities indicated
on April 28th, 2000.

<TABLE>
<CAPTION>
          SIGNATURE                                TITLE
          ---------                                -----
<S>                             <C>
    /S/ JOSEPH J. FOX           Co-Chairman of the Board and Chief Executive
----------------------------    Officer (principal executive officer)
        Joseph J. Fox


       /S/ AVI FOX              Co-Chairman of the Board and President
----------------------------
           Avi Fox


   /S/ JOSEPH A. BARR           Executive Vice President, Chief Financial
----------------------------    Officer (principal financial and accounting
       Joseph A. Barr           officer) and Treasurer


  /S/ ROBERT F. BERNARD         Director
----------------------------
      Robert F. Bernard


  /S/ FREDRIC J. GRABER         Director
----------------------------
      Fredric J. Graber


/S/ D. JONATHAN ROSENBERG       Executive Vice President, Chief Operating
----------------------------    Officer and Director
    D. Jonathan Rosenberg
</TABLE>

                                     II-5
<PAGE>


                               INDEX TO EXHIBITS

<TABLE>
<CAPTION>
Exhibits                                Description
--------    --------------------------------------------------------------------
<S>         <C>
 4.9        The Registrant's 1999 Employee Stock Purchase Plan.

 5          Opinion of Stuart A. Cohn, General Counsel of the Registrant, as to
            the legality of the shares of common stock being offered under the
            Plans.

23.1        Consent of Arthur Andersen LLP.

23.2        Consent of Stuart A. Cohn (contained in his opinion filed as
            Exhibit 5).

24          Power of Attorney (included on the signature page of this
            registration statement).
</TABLE>
[{"type": "S-8", "sequence": "1", "description": "FORM S-8", "secsgml_size_bytes": 21583}]
{"company-data": {"conformed-name": "WEB STREET INC //", "cik": "0001088348", "assigned-sic": "7389", "irs-number": "364212401", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-35902", "film-number": "613610"}, "business-address": {"street1": "510 LAKE COOK ROAD", "city": "DEERFIELD", "state": "IL", "zip": "60015", "phone": "8474444700"}, "mail-address": {"street1": "510 LAKE COOK ROAD", "city": "DEERFIELD", "state": "IL", "zip": "60015"}, "former-company": [{"former-conformed-name": "WEB STREET INC", "date-changed": "19990824"}, {"former-conformed-name": "WEBSTREET COM INC", "date-changed": "19990609"}]}
As filed with the Securities and Exchange Commission on April 28, 2000
                                                           Registration No. 333-
================================================================================

                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549
                             ----------------------

                                    FORM S-8
                             REGISTRATION STATEMENT
                                     Under
                           The Securities Act of 1933

                                WEB STREET, INC.
             (Exact Name of Registrant as Specified in its Charter)

                 Delaware                          36-4212401
      (State or Other Jurisdiction             (I.R.S. Employer
     of Incorporation or Organization)          Identification No.)

                 510 Lake Cook Road, Deerfield, Illinois 60015
        (Address of Principal Executive Offices)      (Zip Code)

               Web Street Financial Group, Inc. Stock Option Plan
                   Web Street, Inc. 1999 Stock Incentive Plan
                Option Agreements Listed on Attached Schedule I
               Web Street, Inc. 1999 Employee Stock Purchase Plan
                           (Full Title of the Plans)

                              Stuart A. Cohn, Esq.
                  Executive Vice President and General Counsel
                 510 Lake Cook Road, Deerfield, Illinois 60015
                    (Name and Address of Agent for Service)
                                 (847) 444-4700
         (Telephone Number, Including Area Code, of Agent for Service)

                                   Copies to:
                               Mark D. Wood, Esq.
                              Adam R. Klein, Esq.
                              Katten Muchin Zavis
                       525 West Monroe Street, Suite 1600
                         Chicago, Illinois  60661-3693
                                 (312) 902-5200
                           ---------------------------

                        CALCULATION OF REGISTRATION FEE
====================================================================================================================
                                                           Proposed Maximum     Proposed Maximum
                                          Amount To Be      Offering Price    Aggregate Offering       Amount Of
Title Of Securities To Be Registered     Registered (1)        Per Share             Price          Registration Fee
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (Stock Option Plan)..................  1,298,000 shares         $6.47(2)          $ 8,398,060(2)           $2,335
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (1999 Stock Incentive Plan)..........  4,000,000 shares         $8.19(3)          $17,216,671(3)           $4,786
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (Option Agreements)..................    569,377 shares         $ .06(4)          $    34,163(4)           $   10
--------------------------------------------------------------------------------------------------------------------
Common Stock, $0.01 par value
 (1999 Stock Purchase Plan)...........  1,000,000 shares         $3.85(5)          $ 3,850,000(5)           $1,070
--------------------------------------------------------------------------------------------------------------------
         Total........................  6,867,377 shares            --                      --              $8,201
====================================================================================================================
(1) This registration statement also covers an indeterminate number of shares of
    Web Street, Inc. Common Stock that may be issuable by reason of stock
    splits, stock dividends or similar transactions in accordance with Rule 416
    under the Securities Act of 1933.

(2) Based upon the weighted average exercise price for the currently outstanding
    options granted under this plan. These amounts are used solely for the
    purpose of calculating the registration fee pursuant to Rule 457(h)(1) under
    the Securities Act.

(3) Based upon (i) the weighted average exercise price of $8.19 per share for
    currently outstanding options to purchase 418,588 shares of Common Stock
    granted under this plan and (ii) the average of the high and low sales
    prices of the Common Stock as reported on the Nasdaq National Market on
    April 26, 2000, which was $3.85, with respect to 3,581,412 shares of Common
    Stock which may be granted under this plan. These amounts are used solely
    for the purpose of calculating the registration fee pursuant to Rules
    457(h)(1) and 457(c) under the Securities Act.

(4) Based upon the weighted average exercise price for the currently outstanding
    options granted under these agreements. These amounts are used solely for
    the purpose of calculating the registration fee pursuant to Rule 457(h)(1)
    under the Securities Act.

(5) Based on the average of the high and low sales prices of the Common Stock as
    reported on the Nasdaq National Market on April 26, 2000. These amounts
    are used solely for the purpose of calculating the registration fee pursuant
    to Rule 457(c) under the Securities Act.
================================================================================
SCHEDULE I
                                   ----------

     Option Agreements between Web Street Financial Group, Inc. and the
     following employees and consultants:

     Fred Allen
     Manuel Calderon
     Ryan Carpel
     Stuart Cohn
     Barbara Escobar
     Paul Gakhal
     Michael Graf
     Michael Grimes
     Jason Hersh
     Vanesa Horton
     Gary Just
     William Mania
     Christopher Mazzacono
     Melvin Pinkham
     D. Jonathan Rosenberg
     Jonah Rosenberg
     Robert Rosenberg
     Jeffrey Schulhof
     Alan Seleman
     Jeffrey Williams
     Tom Wilson
     Saul Zadik
     Steve Zakrzewski

                                     I-1
PART I
             INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS

     The information called for in Part I of Form S-8 is currently included in
the prospectuses for the Web Street Financial Group, Inc. Stock Option Plan, the
Web Street, Inc. 1999 Stock Incentive Plan, the option agreements listed on the
attached Schedule I and the Web Street, Inc. 1999 Employee Stock Purchase Plan
(collectively, the "Plans"), and is not being filed with, or included in, this
Form S-8 in accordance with the rules and regulations of the SEC. Web Street
will not issue any additional options under the Web Street Financial Group, Inc.
Stock Option Plan or the option agreements listed on the attached Schedule I.
Web Street Financial Group, Inc. is the former name of Web Street, Inc.

                                      I-2
PART II
              INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3.  Incorporation of Documents by Reference.

     The following documents filed by the Registrant with the SEC are
incorporated by reference in this registration statement:

     (a)  The Registrant's Annual Report on Form 10-K for the fiscal year ended
          December 31, 1999; and

     (b)  The description of the Registrant's common stock in the Registrant's
          Registration Statement on Form 8-A filed on October 18, 1999 pursuant
          to the Securities Exchange Act of 1934, and all subsequent amendments
          and reports filed for the purpose of updating the description.

     In addition, all documents that the Registrant files pursuant to Sections
13(a), 13(c), 14 or 15(d) of the Exchange Act after the date of this
registration statement and before the filing of a post-effective amendment
indicating that all securities offered pursuant to this registration statement
have been sold or deregistering all the securities then remaining unsold shall
be deemed to be incorporated by reference in this registration statement and to
be part of this registration statement from the date of filing of those
documents. Any statement contained in a document incorporated or deemed to be
incorporated by reference in this registration statement shall be deemed to be
modified or superseded for purposes of this registration statement to the extent
that a statement contained in this registration statement or in any subsequently
filed document which also is or is deemed to be incorporated by reference in
this registration statement modifies or supersedes that statement.

     The Registrant will provide without charge to each person who has received
a copy of any prospectus to which this registration statement relates, upon the
written or oral request of that person, a copy of any or all the documents that
have been or may be incorporated by reference into this registration statement,
other than exhibits to those documents, unless the exhibits are incorporated by
reference in those documents. Written requests for copies should be directed to
the Registrant's principal executive offices at 510 Lake Cook Road, Deerfield,
Illinois 60015, Attention: Corporate Secretary. Telephone requests for copies
should be directed to the Registrant's Corporate Secretary at (847) 444-4700.

Item 4. Description of Securities.

     Not applicable.

Item 5. Interests of Named Experts and Counsel.

     Not applicable.

Item 6. Indemnification of Directors and Officers.

     As permitted by the Delaware General Corporation Law, the Registrant's
Amended and Restated Certificate of Incorporation contains provisions that
eliminate the personal liability of the Registrant's directors to the Registrant
or its stockholders for monetary damages for the breach or alleged breach of
their fiduciary duty as a director, except for liability for:

                                     II-1
.    any breach of their duty of loyalty to the Registrant or its
          stockholders;

     .    acts or omissions not in good faith or which involve intentional
          misconduct or a knowing violation of law;

     .    willful or negligent conduct in paying dividends or repurchasing stock
          out of other than lawfully available funds; and

     .    any transaction from which the director derived an improper personal
          benefit.

     The Registrant's Amended and Restated Certificate of Incorporation also
contains provisions that require the Registrant to indemnify its directors and
permit the Registrant to indemnify its officers and employees to the fullest
extent permitted by Delaware corporate law. However, the Registrant is not
obligated to indemnify a person:

     .    with respect to proceedings, claims or actions initiated or brought
          voluntarily by the person and not by way of defense; and

     .    for any amounts paid in settlement of an action indemnified against by
          the Registrant without its prior written consent.

The Registrant has entered into indemnity agreements with each of its directors
and executive officers providing for this indemnification and containing the
Registrant's covenant to maintain directors' and officers' liability insurance.

     Reference is made to Section 145 of the General Corporation Law of the
State of Delaware which provides for indemnification of directors and officers
in certain circumstances.

Item 7. Exemption from Registration Claimed.

     Not applicable.

Item 8. Exhibits.

     4.1  The Registrant's Amended and Restated Certificate of Incorporation,
          incorporated by reference to Exhibit 3.1 to the Registrant's Annual
          Report on Form 10-K for the fiscal year ended December 31, 1999
          (the "1999 10-K").

     4.2  The Registrant's Amended and Restated Bylaws, incorporated by
          reference to Exhibit 3.2 to the 1999 10-K.

     4.3  Specimen stock certificate representing common stock, incorporated by
          reference to Exhibit 4 to the Registrant's Registration Statement on
          Form S-1, as amended (Registration Statement No. 333-85849) (the
          "IPO Registration Statement").

     4.4  Web Street Financial Group, Inc. Stock Option Plan, incorporated by
          reference to Exhibit 10.1 to the IPO Registration Statement.

     4.5  Form of Option Agreement under the Stock Option Plan, incorporated by
          reference to Exhibit 10.2 to the IPO Registration Statement.

                                     II-2
4.6  Form of Option Agreement with various employees and consultants prior
          to the Stock Option Plan, incorporated by reference to Exhibit 10.3 to
          the IPO Registration Statement.

     4.7  The Registrant's 1999 Stock Incentive Plan, incorporated by reference
          to Exhibit 10.4 to the IPO Registration Statement.

     4.8  Form of Option Agreement under the 1999 Stock Incentive Plan,
          incorporated by reference to Exhibit 10.5 to the IPO Registration
          Statement.

     4.9  The Registrant's 1999 Employee Stock Purchase Plan.

     5    Opinion of Stuart A. Cohn, General Counsel of the Registrant, as to
          the legality of the shares of common stock being offered under the
          Plans.

    23.1  Consent of Arthur Andersen LLP.

    23.2  Consent of Stuart A. Cohn (contained in his opinion filed as
          Exhibit 5).

    24    Power of Attorney (included on the signature page of this registration
          statement).

                                     II-3
Item 9. Undertakings.

     1.   The Registrant hereby undertakes:

          (a)  To file, during any period in which offers or sales are being
     made, a post-effective amendment to this 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 the 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; 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)(i) and (a)(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 by the Registrant
     pursuant to Section 13 or Section 15(d) of the Exchange Act that are
     incorporated by reference in the registration statement.

          (b)  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.

          (c)  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.

     2.   The Registrant hereby undertakes that, for the purpose of determining
any liability under the Securities Act, each filing of its 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 reference in the
registration statement 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.

     3.   Insofar as indemnification for liabilities arising under the
Securities Act may be permitted to the Registrant's directors, officers and
controlling persons pursuant to the foregoing provisions or otherwise, the
Registrant has been advised that in the opinion of the SEC 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-4
SIGNATURES

     Pursuant to the requirements of the Securities Act, 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 Deerfield, State of Illinois, on this 28th day of
April, 2000.

                                     WEB STREET, INC.

                                     By: /S/ JOSEPH J. FOX
                                         ---------------------------------------
                                         Joseph J. Fox
                                         Chief Executive Officer and Co-Chairman
                                         of the Board

                               POWER OF ATTORNEY

     Each person whose signature appears below hereby constitutes and appoints
Joseph J. Fox, Stuart A. Cohn and Mark D. Wood, and each of them, his true and
lawful attorneys-in-fact and agents, with full power of substitution, to sign on
his behalf, individually and in each capacity stated below, all amendments and
post-effective amendments to this registration statement on Form S-8 and to file
the same, with all exhibits thereto and any other documents in connection
therewith, with the SEC under the Securities Act, granting unto said
attorneys-in-fact and agents 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 and to all intents and purposes as each might or could do in
person, hereby ratifying and confirming each act that said attorneys-in-fact and
agents may lawfully do or cause to be done by virtue thereof.

     Pursuant to the requirements of the Securities Act, this registration
statement has been signed by the following persons in the capacities indicated
on April 28th, 2000.
SIGNATURE                                TITLE
          ---------                                -----
/S/ JOSEPH J. FOX           Co-Chairman of the Board and Chief Executive
----------------------------    Officer (principal executive officer)
        Joseph J. Fox

       /S/ AVI FOX              Co-Chairman of the Board and President
----------------------------
           Avi Fox

   /S/ JOSEPH A. BARR           Executive Vice President, Chief Financial
----------------------------    Officer (principal financial and accounting
       Joseph A. Barr           officer) and Treasurer

  /S/ ROBERT F. BERNARD         Director
----------------------------
      Robert F. Bernard

  /S/ FREDRIC J. GRABER         Director
----------------------------
      Fredric J. Graber

/S/ D. JONATHAN ROSENBERG       Executive Vice President, Chief Operating
----------------------------    Officer and Director
    D. Jonathan Rosenberg
II-5
INDEX TO EXHIBITS
Exhibits                                Description
--------    --------------------------------------------------------------------
4.9        The Registrant's 1999 Employee Stock Purchase Plan.

 5          Opinion of Stuart A. Cohn, General Counsel of the Registrant, as to
            the legality of the shares of common stock being offered under the
            Plans.

23.1        Consent of Arthur Andersen LLP.

23.2        Consent of Stuart A. Cohn (contained in his opinion filed as
            Exhibit 5).

24          Power of Attorney (included on the signature page of this
            registration statement).