<PAGE>
                                                                  EXHIBIT 10.101


                                 FIFTH AMENDMENT
                                     TO THE
                     COMPUWARE CORPORATION ESOP/401(k) PLAN
                (AS AMENDED AND RESTATED EFFECTIVE APRIL 1, 2004)



WHEREAS, Compuware Corporation (the "Company") has established and maintains the
Compuware Corporation ESOP/401(k) Plan (the "Plan), originally effective as of
April 1, 1986, as most recently amended and restated effective as of April 1,
2004, and as subsequently amended by First, Second, Third, and Fourth
Amendments; and

WHEREAS, pursuant to Section 11.01, the Plan Administrator has been delegated
the authority to amend the Plan; and

WHEREAS, the Plan Administrator desires to amend the Plan to provide for a
special allocation of Company contributions and forfeitures for the plan year
ending March 31, 2007; and

WHEREAS, the Plan Administrator desires to amend the Plan in order to accomplish
the merger of the ProviderLink 401(k) Plan; and

WHEREAS, the Plan Administrator desires to amend the Plan to clarify the
application of the two-year restriction on in-service withdrawals or transfers
from a participant's Company Contribution Account;

NOW THEREFORE, IN CONSIDERATION OF THE PREMISES, the Plan is amended as follows:

1. Section 2.45, "Merge Date," is amended, effective May 23, 2006, by adding the
following:

                   August 2, 2006           ProviderLink 401(k) Plan

2. Section 2.46, "Merged Plans," is amended, effective May 23, 2006, by adding
the following:

                  ProviderLink 401(k) Plan

3. Subsection (a)(2)(C) of Section 5.01(a), INVESTMENT OPTIONS, is amended and
restated, effective April 1, 2006, to read as follows:

         (C) regardless of an Active or Former Active Participant's age or
         service, the funds are attributable to contributions that have been
         allocated to his or her Company Contribution Account for at least two
         anniversary years from the date the recordkeeper performed the
         allocation for the Plan Year, which date is no earlier than the date
         the contribution was deposited into the Trust. The two year

<PAGE>

         restriction shall not apply to a Former Active Participant who no
         longer is an Employee.

4. Section 4.07, COMPANY DISCRETIONARY CONTRIBUTIONS, is amended, effective May
22, 2006, by adding a new subsection (h) that reads as follows:

         (f) The Company shall make a special mid-year contribution and
         allocation of Company Stock in an amount sufficient so that when added
         to forfeitures of Company Stock available for reallocation, each
         Participant who satisfies the eligibility requirements described in (1)
         and (2) of this subsection shall receive an allocation of 100 shares of
         Company Stock. To be eligible for this special allocation, as of May
         22, 2006, a Participant must be:

                  (1) a U.S.-Based Employee; and

                  (2) an Active Participant, including an Active Participant on
         leave of absence as identified in the Company's Human Resources
         Information System, but excluding


                      (A) full-time hourly Employees unless they are on Services
         Microsoft Direct Cost assignment;

                      (B) Employees classified by the Company as Tier I or
         Tier II Executives covered under the Employer's fiscal year 2007
         Executive Bonus Plan; and

                      (C) Employees who are summer interns hired for short-term
         employment between post-secondary school semesters.

IN WITNESS WHEREOF, the Company has caused this Fifth Amendment to the Compuware
Corporation ESOP/401(k) Plan to be executed by its duly authorized
representative this 23rd day of May, 2006.



                                                     COMPUWARE CORPORATION

                                                     By:  /s/  Kathy Igoe
                                                          ----------------------

                                                     Its:     Secretary
                                                           ---------------------