<PAGE>

    As filed with the Securities and Exchange Commission on August 30, 2000
                                                   Registration No. 333-________

                      SECURITIES AND EXCHANGE COMMISSION
                           Washington, D. C.  20549

                                   FORM S-8

            REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                          MICROSTRATEGY INCORPORATED
            (Exact Name of Registrant as Specified in Its Charter)

         Delaware                                            51-0323571
(State or Other Jurisdiction of                           (I.R.S. Employer
Incorporation or Organization)                         Identification Number)

8000 Towers Crescent Drive
Vienna, Virginia                                                22182
(Address of Principal Executive Offices)                      (Zip Code)

                           1997 DIRECTOR OPTION PLAN
                           (Full Title of the Plan)

                             Mr. Michael J. Saylor
                     President and Chief Executive Officer
                          MicroStrategy Incorporated
                          8000 Towers Crescent Drive
                               Vienna, VA 22182
                    (Name and Address of Agent for Service)

                                (703) 848-8600
         (Telephone Number, Including Area Code, of Agent for Service)


                        CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>
==================================================================================================================
                                                  Proposed              Proposed
                            Amount to             Maximum               Maximum
 Title of Securities to        be               Offering Price          Aggregate               Amount of
    be Registered           Registered            Per Share           Offering Price         Registration Fee
--------------------------------------------------------------------------------------------------------------
<S>                       <C>               <C>                      <C>                     <C>
Class A Common Stock,
 par value $0.001 per
 share                     200,000 shares         $ 35.02(1)           $ 7,004,390(1)            $ 1,850.00
==================================================================================================================
</TABLE>


(1)  For purposes of computing the registration fee only.  Pursuant to Rule
     457(c) and Rule 457(h) under the Securities Act of 1933, as amended, the
     Proposed Maximum Offering Price Per Share is based upon (i) with respect to
     40,000 shares that may be acquired pursuant to stock options granted by
     MicroStrategy Incorporated (the "Company") under the MicroStrategy
     Incorporated 1997 Director Option Plan, as amended (the "Option Plan")
     prior to the date of this Registration Statement, the actual price at which
     such stock options may be exercised; and (ii) with respect to the remaining
     160,000 shares that may be acquired pursuant to stock options that may be
     granted by the Company under the Option Plan from time to time after the
     date hereof, $25.8125 per share, which represents the average of the high
     and low prices reported on the Nasdaq Stock Market for shares of the Class
     A Common Stock on August 23, 2000.


<PAGE>

                    STATEMENT OF INCORPORATION BY REFERENCE

     This Registration Statement on Form S-8 incorporates by reference the
contents of the Registration Statement on Form S-8, File No. 333-58189, filed by
MicroStrategy Incorporated (the "Registrant") on June 30, 1998, relating to the
Registrant's 1997 Director Option Plan.


<PAGE>
                                  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 Vienna, Virginia on August 30, 2000.


                                MICROSTRATEGY INCORPORATED


                                By: /s/ Michael J. Saylor
                                    ------------------------------------
                                    Michael J. Saylor
                                    Chairman of the Board,
                                    Chief Executive Officer and President



                       POWER OF ATTORNEY AND SIGNATURES

     Each person whose signature appears below constitutes and appoints Michael
J. Saylor, Sanju K. Bansal, Eric F. Brown and Jonathan F. Klein as his true and
lawful attorney-in-fact and agent, with full power of substitution and
resubstitution, for such person and in his name, place and stead, in any and all
capacities, to sign any or all further 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
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
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 thereof.

<PAGE>

     Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons in the
capacities and on the dates indicated.

<TABLE>
<CAPTION>
Signatures                             Title                                             Date
----------                             -----                                             ----
<S>                                    <C>                                         <C>
    /s/ Michael J. Saylor              Chairman of the Board, Chief Executive      August 30, 2000
-------------------------------------  Officer and President (Principal
   Michael J. Saylor                   Executive Officer)

   /s/ Eric F. Brown                   Vice President, Finance and Chief           August 24, 2000
-------------------------------------  Financial Officer (Principal Financial
   Eric F. Brown                       and Accounting Officer)

   /s/Sanju K. Bansal                  Director                                    August 23, 2000
-------------------------------------
   Sanju K. Bansal

   /s/ Frank A. Ingari                 Director                                    August 24, 2000
-------------------------------------
   Frank A. Ingari

   /s/ Jonathan J. Ledecky             Director                                    August 27, 2000
-------------------------------------
   Jonathan J. Ledecky

   /s/ John W. Sidgmore                Director                                    August 28, 2000
-------------------------------------
   John W. Sidgmore

   /s/ Ralph S. Terkowitz              Director                                    August 28, 2000
-------------------------------------
   Ralph S. Terkowitz

</TABLE>

<PAGE>

EXHIBIT INDEX


Exhibit
Number              Description
-------             -----------


  4.1*    Specimen Certificate for Class A Common Stock of the Registrant

  5.1     Opinion of Hale and Dorr LLP

 23.1     Consent of Hale and Dorr LLP (included in Exhibit 5.1)

 23.2     Consent of PricewaterhouseCoopers LLP

 24       Power of Attorney (included in the signature pages of this
          Registration Statement)


*    Incorporated herein by reference to the Registrant's Registration Statement
     on Form S-1, as amended (File No. 333-49899).
[{"type": "S-8", "sequence": "1", "filename": "0001.txt", "description": "1997 DIRECTOR OPTION PLAN", "secsgml_size_bytes": 7971}]
{"company-data": {"conformed-name": "MICROSTRATEGY INC", "cik": "0001050446", "assigned-sic": "7372", "irs-number": "510323571", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-44846", "film-number": "713975"}, "business-address": {"street1": "8000 TOWERS CRESCENT DR", "city": "VIENNA", "state": "VA", "zip": "22182", "phone": "7038488600"}, "mail-address": {"street1": "8000 TOWERS CRESCENT DR", "city": "VIENNA", "state": "VA", "zip": "22182"}}
As filed with the Securities and Exchange Commission on August 30, 2000
                                                   Registration No. 333-________

                      SECURITIES AND EXCHANGE COMMISSION
                           Washington, D. C.  20549

                                   FORM S-8

            REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                          MICROSTRATEGY INCORPORATED
            (Exact Name of Registrant as Specified in Its Charter)

         Delaware                                            51-0323571
(State or Other Jurisdiction of                           (I.R.S. Employer
Incorporation or Organization)                         Identification Number)

8000 Towers Crescent Drive
Vienna, Virginia                                                22182
(Address of Principal Executive Offices)                      (Zip Code)

                           1997 DIRECTOR OPTION PLAN
                           (Full Title of the Plan)

                             Mr. Michael J. Saylor
                     President and Chief Executive Officer
                          MicroStrategy Incorporated
                          8000 Towers Crescent Drive
                               Vienna, VA 22182
                    (Name and Address of Agent for Service)

                                (703) 848-8600
         (Telephone Number, Including Area Code, of Agent for Service)

                        CALCULATION OF REGISTRATION FEE
==================================================================================================================
                                                  Proposed              Proposed
                            Amount to             Maximum               Maximum
 Title of Securities to        be               Offering Price          Aggregate               Amount of
    be Registered           Registered            Per Share           Offering Price         Registration Fee
--------------------------------------------------------------------------------------------------------------
Class A Common Stock,
 par value $0.001 per
 share                     200,000 shares         $ 35.02(1)           $ 7,004,390(1)            $ 1,850.00
==================================================================================================================
(1)  For purposes of computing the registration fee only.  Pursuant to Rule
     457(c) and Rule 457(h) under the Securities Act of 1933, as amended, the
     Proposed Maximum Offering Price Per Share is based upon (i) with respect to
     40,000 shares that may be acquired pursuant to stock options granted by
     MicroStrategy Incorporated (the "Company") under the MicroStrategy
     Incorporated 1997 Director Option Plan, as amended (the "Option Plan")
     prior to the date of this Registration Statement, the actual price at which
     such stock options may be exercised; and (ii) with respect to the remaining
     160,000 shares that may be acquired pursuant to stock options that may be
     granted by the Company under the Option Plan from time to time after the
     date hereof, $25.8125 per share, which represents the average of the high
     and low prices reported on the Nasdaq Stock Market for shares of the Class
     A Common Stock on August 23, 2000.
STATEMENT OF INCORPORATION BY REFERENCE

     This Registration Statement on Form S-8 incorporates by reference the
contents of the Registration Statement on Form S-8, File No. 333-58189, filed by
MicroStrategy Incorporated (the "Registrant") on June 30, 1998, relating to the
Registrant's 1997 Director Option Plan.
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 Vienna, Virginia on August 30, 2000.

                                MICROSTRATEGY INCORPORATED

                                By: /s/ Michael J. Saylor
                                    ------------------------------------
                                    Michael J. Saylor
                                    Chairman of the Board,
                                    Chief Executive Officer and President

                       POWER OF ATTORNEY AND SIGNATURES

     Each person whose signature appears below constitutes and appoints Michael
J. Saylor, Sanju K. Bansal, Eric F. Brown and Jonathan F. Klein as his true and
lawful attorney-in-fact and agent, with full power of substitution and
resubstitution, for such person and in his name, place and stead, in any and all
capacities, to sign any or all further 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
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
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 thereof.
Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons in the
capacities and on the dates indicated.
Signatures                             Title                                             Date
----------                             -----                                             ----
/s/ Michael J. Saylor              Chairman of the Board, Chief Executive      August 30, 2000
-------------------------------------  Officer and President (Principal
   Michael J. Saylor                   Executive Officer)

   /s/ Eric F. Brown                   Vice President, Finance and Chief           August 24, 2000
-------------------------------------  Financial Officer (Principal Financial
   Eric F. Brown                       and Accounting Officer)

   /s/Sanju K. Bansal                  Director                                    August 23, 2000
-------------------------------------
   Sanju K. Bansal

   /s/ Frank A. Ingari                 Director                                    August 24, 2000
-------------------------------------
   Frank A. Ingari

   /s/ Jonathan J. Ledecky             Director                                    August 27, 2000
-------------------------------------
   Jonathan J. Ledecky

   /s/ John W. Sidgmore                Director                                    August 28, 2000
-------------------------------------
   John W. Sidgmore

   /s/ Ralph S. Terkowitz              Director                                    August 28, 2000
-------------------------------------
   Ralph S. Terkowitz
EXHIBIT INDEX

Exhibit
Number              Description
-------             -----------

  4.1*    Specimen Certificate for Class A Common Stock of the Registrant

  5.1     Opinion of Hale and Dorr LLP

 23.1     Consent of Hale and Dorr LLP (included in Exhibit 5.1)

 23.2     Consent of PricewaterhouseCoopers LLP

 24       Power of Attorney (included in the signature pages of this
          Registration Statement)

*    Incorporated herein by reference to the Registrant's Registration Statement
     on Form S-1, as amended (File No. 333-49899).