Document:

<PAGE>   1
                                                                   Exhibit 10.88

                                                                  EXECUTION COPY
                                                                  --------------

                             THE PIONEER GROUP, INC.

                                CREDIT AGREEMENT

                                Amendment No. 10
                                ----------------

         This Agreement, dated as of December 13, 1999, is among The Pioneer
Group, Inc., a Delaware corporation (the "Company"), certain of its subsidiaries
listed on the signature pages hereto, the Lenders (as defined in the Credit
Agreement referenced below) and BankBoston, N.A., f/k/a The First National Bank
of Boston, as agent (the "Agent") for itself and the other Lenders. The parties
agree as follows:

1. Reference to Credit Agreement; Definitions. Reference is made to the Credit
Agreement dated as of June 6, 1996, among the Company, certain of its
subsidiaries, the Lenders and the Agent (as amended, modified and in effect
prior to giving effect to this Agreement, the "Credit Agreement"). Terms defined
in the Credit Agreement as amended hereby (the "Amended Credit Agreement") and
not otherwise defined herein are used herein with the meanings so defined.
Except as the context otherwise explicitly requires, the capitalized terms
"Section" and "Exhibit" refer to sections hereof and exhibits hereto.

2. Amendments to Credit Agreement. Subject to all of the terms and conditions
hereof and in reliance upon the representations and warranties set forth in
Section 3, the Credit Agreement is amended as follows, effective upon the date
(the "Amendment Date") that the conditions specified in Section 4 are satisfied,
which conditions must be satisfied no later than December 13, 1999 or this
Agreement shall be of no force or effect:

         2.1 Amendment of Section 1.80. Section 1.80 of the Credit Agreement is
amended to read in its entirety as follows:

         "1.80. "Guarantor" means the Company and each of the Core Mutual Fund
         Subsidiaries (initially other than the Excluded Subsidiaries) and other
         Subsidiaries, including the Excluded Subsidiaries, from time to time
         becoming party to this Agreement as a Guarantor, provided, however,
         that effective on and after January 1, 1999, Pioneer Management
         (Ireland) Ltd. shall no longer be a Guarantor."

         2.2 Amendment of Section 1.106. Section 1.106 of the Credit Agreement
is amended to read in its entirety as follows:

                  "1.106 "Obligors" means (i) before January 1, 1999, the
                  Borrowers and the Guarantors and (ii) on and after January 1,
                  1999, the Borrowers, the Guarantors and Pioneer Management
                  (Ireland) Ltd."

                                      -1-
<PAGE>   2

         2.3. Amendment to Section 6.2. Section 6.2 of the Credit Agreement is
amended to read in its entirety as follows:

         "6.2. Continuing Obligation. Each Guarantor acknowledges that the
         Lenders have entered into this Agreement (and, to the extent that the
         Lenders may enter into any future Credit Document, will have entered
         into such agreement) in reliance on this Section 6 being a continuing
         irrevocable agreement, and such Guarantor agrees that its guarantee may
         not be revoked in whole or in part without the approval of the Required
         Lenders. The obligations of the Guarantors hereunder shall terminate
         when the commitment of the Lenders to extend credit under this
         Agreement shall have terminated and all of the Credit Obligations have
         been indefeasibly paid in full in immediately available funds and
         discharged; provided, however, that

                           (i) if a claim is made upon the Lenders at any time
                  for repayment or recovery of any amounts or any property
                  received by the Lenders from any source on account of any of
                  the Credit Obligations and the Lenders repay or return any
                  amounts or property so received (including interest thereon to
                  the extent required to be paid by the Lenders) or

                           (ii) if the Lenders become liable for any part of
                  such claim by reason of (a) any judgment or order of any court
                  or administrative authority having competent jurisdiction or
                  (b) any settlement or compromise of any such claim,

then the Guarantors shall remain liable under this Agreement for the amounts so
repaid or returned or the amounts for which the Lenders become liable (such
amounts being deemed part of the Credit Obligations) to the same extent as if
such amounts had never been received by the Lenders, notwithstanding any
termination hereof or the cancellation of any instrument or agreement evidencing
any of the Credit Obligations. The Guarantors shall, not later than five days
after receipt of notice from the Agent, pay to the Agent an amount equal to the
amount of such repayment or return for which the Lenders have so become liable.
Payments hereunder by a Guarantor may be required by the Agent or the Required
Lenders on any number of occasions."

3. Representations and Warranties. In order to induce the Lenders to enter into
this Agreement, each of the Company and the Guarantors represents and warrants
to each of the Lenders that:

         3.1. Legal Existence, Organization. Each of the Company and its
Subsidiaries is duly organized and validly existing and in good standing under
the laws of the jurisdiction of its incorporation, with all power and authority,
corporate or otherwise, necessary to (i) enter into and perform this Agreement,
the Amended Credit Agreement and each other Credit Document to which it is party
and (ii) own its properties and carry on the business now conducted or proposed
to be conducted by it. Each of the Company and its Subsidiaries has taken, or
shall have taken on or prior to the Amendment Date, all corporate or other
action required to make the provisions

                                      -2-
<PAGE>   3

of this Agreement, the Amended Credit Agreement and each other Credit Document
to which it is party the valid and enforceable obligations they purport to be.

         3.2. Enforceability. The Company and each of its Subsidiaries which are
signatories hereto have duly executed and delivered this Agreement. Each of this
Agreement and the Amended Credit Agreement is the legal, valid and binding
obligation of the Company and such Subsidiaries and is enforceable in accordance
with its terms.

         3.3. No Legal Obstacle to Agreements. Neither the execution, delivery
or performance of this Agreement, nor the performance of the Amended Credit
Agreement, nor the consummation of any other transaction referred to in or
contemplated by this Agreement, nor the fulfillment of the terms hereof or
thereof, has constituted or resulted in or will constitute or result in:

         (1) any breach or termination of the provisions of any agreement,
         instrument, deed or lease to which the Company or any Subsidiary is a
         party or by which it is bound, or of the Charter or By-laws of the
         Company or any Subsidiary;

         (2) the violation of any law, judgment, decree or governmental order,
         rule or regulation applicable to the Company or any Subsidiary;

         (3) the creation under any agreement, instrument, deed or lease of any
         Lien upon any of the assets of the Company or any Subsidiary; or

         (4) any redemption, retirement or other repurchase obligation of the
         Company or any Subsidiary under any Charter, By-law, agreement,
         instrument, deed or lease.

No approval, authorization or other action by, or declaration to or filing with,
any governmental or administrative authority or any other Person is required to
be obtained or made by the Company or any Subsidiary in connection with the
execution, delivery and performance of this Agreement or the performance of the
Amended Credit Agreement, or the consummation of the transactions contemplated
hereby or thereby.

         3.4. No Default. Prior to and after giving effect to the amendments set
forth in Section 2, no Default will exist.

         3.5. Incorporation of Representations and Warranties. The
representations and warranties set forth in Section 8 of the Credit Agreement,
or in the case of the Guarantors, Section 6.6 of the Credit Agreement are true
and correct on the date hereof as if originally made on and as of the date
hereof (except to the extent any representation or warranty refers to a specific
earlier date).

                                      -3-
<PAGE>   4

         3.6. Income of Released Guarantor. The Company projects that the
operating income of Pioneer Management (Ireland) Ltd. for the fiscal year 1999
and fiscal year 2000 will be less than $2 million.

4. Conditions. The effectiveness of this Agreement shall be subject to the
satisfaction of the following conditions:

         4.1. Amendment to Note Agreement. The Note Agreement dated August 14,
1997, among the Company and its Subsidiaries listed as Guarantors (including
other Subsidiaries of the Company that from time to time become party thereto)
and the Travelers Insurance Company shall have been amended to release Pioneer
Management (Ireland) Ltd. as a Guarantor on terms and conditions shall be
satisfactory to the Lenders.

         4.2. Investment Assets Under Management. On the Amendment Date, the
aggregate investment assets under management by the Company and its Subsidiaries
shall equal or exceed $20,000,000,000, and the Company shall have furnished to
the Agent on such date a certificate to such effect signed by an Executive
Officer or a Financial Officer.

         4.3.  Fees.

         The Company shall have paid all fees due to the Agent or other lenders
and all reasonable fees and disbursements of Ropes & Gray, special counsel to
the Lenders.

         4.4. Officer's Certificate. The representations and warranties
contained in Section 3 shall be true and correct as of the Amendment Date with
the same force and effect as though originally made on and as of such date; no
Default shall exist on the Amendment Date immediately prior to and after giving
effect to this Agreement; as of the Amendment Date, no Material Adverse Change
shall have occurred; and the Company shall have furnished to the Agent on the
Amendment Date a certificate to these effects, in substantially the form of
Exhibit 4.5, signed by an Executive Officer or a Financial Officer.

         4.5. Proper Proceedings. All proper corporate proceedings shall have
been taken by each of the Company and the Subsidiaries to authorize this
Agreement, the Amended Credit Agreement and the transactions contemplated hereby
and thereby. The Agent shall have received copies of all documents, including
legal opinions of counsel and records of corporate proceedings which the Agent
may have requested in connection therewith, such documents, where appropriate,
to be certified by proper corporate or governmental authorities.

         4.6. Legal Opinion. The Lenders shall have received from Robert P.
Nault, General Counsel of The Pioneer Group, Inc., Counsel of the Company and
the Subsidiaries, an opinion with respect to the transactions contemplated by
this Amendment, which opinion shall be in form and substance satisfactory to the
Lenders.

                                      -4-
<PAGE>   5

         4.7. Execution by Lenders. The Lenders owning 100% of the Percentage
Interests under the Credit Agreement shall have executed and delivered this
Agreement to the Company.

5. Further Assurances. Each of the Company and the Subsidiaries will, promptly
upon request of the Agent from time to time, execute, acknowledge and deliver,
and file and record, all such instruments and notices, and take all such action,
as the Agent deems necessary or advisable to carry out the intent and purposes
of this Agreement.

6. General. The Amended Credit Agreement and all of the other Credit Documents
are each confirmed as being in full force and effect. This Agreement, the
Amended Credit Agreement and the other Credit Documents referred to herein or
therein constitute the entire understanding of the parties with respect to the
subject matter hereof and thereof and supersede all prior and current
understandings and agreements, whether written or oral, with respect to such
subject matter. The invalidity or unenforceability of any provision hereof shall
not affect the validity or enforceability of any other term or provision hereof.
The headings in this Agreement are for convenience of reference only and shall
not alter, limit or otherwise affect the meaning hereof. Each of this Agreement
and the Amended Credit Agreement is a Credit Document and may be executed in any
number of counterparts, which together shall constitute one instrument, and
shall bind and inure to the benefit of the parties and their respective
successors and assigns, including as such successors and assigns all holders of
any Note. THIS AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH
THE LAWS (OTHER THAN THE CONFLICT OF LAWS RULES) OF THE COMMONWEALTH OF
MASSACHUSETTS.

                                      -5-

<PAGE>   6

Each of the undersigned has caused this Agreement to be executed and delivered
by its duly authorized officer as an agreement under seal as of the date first
above written.

THE PIONEER GROUP, INC.
                                                PIONEERING SERVICES CORPORATION

By: /s/  Eric W. Reckard                        By: /s/ Eric W. Reckard
    --------------------------                      -----------------------
Title: Executive Vice President                       Title: Treasurer
      Chief Financial Officer and Treasurer
60 State Street                                 60 State Street
Boston, Massachusetts 02109-1820                Boston, Massachusetts 02109-1820

PIONEER INVESTMENT MANAGEMENT, INC.

By: /s/ Eric W. Reckard
    ----------------------------
   Title: Treasurer
60 State Street
Boston, Massachusetts 02109-1820

PIONEER MANAGEMENT (IRELAND) LTD.

By: /s/ John F. Cogan, Jr.
    ----------------------------
   Title: Director
60 State Street
Boston, Massachusetts 02109-1820

PIONEER FUNDS DISTRIBUTOR, INC.

By: /s/ Eric W. Reckard
    ----------------------------
   Title: Treasurer
60 State Street
Boston, Massachusetts 02109-1820

                                      -6-

<PAGE>   7

                                BANKBOSTON, N.A.

                                By:/s/ Matthew Steinaway
                                   ----------------------------
                                   Title: Vice President

                                   Financial Institutions Division
                                   100 Federal Street - 15th Floor
                                   Boston, Massachusetts 02110
                                   Telecopy: (617) 434-1537
                                   Telex: 940581

                                THE BANK OF NEW YORK

                                By:/s/ Michael B. Scaduto
                                   ----------------------------
                                   Title: Vice President

                                   One Wall Street, 17th Floor
                                   Mutual Fund Banking Division
                                   New York, NY 10286
                                   Telecopy: (212) 635-6348
                                   Telex:

                                SOCIETE GENERALE

                                By:/s/ Daniel P. Kelly
                                   Title: Vice President

                                   1221 Avenue of the Americas
                                   New York, New York 10020
                                   Telecopy: (212) 278-7153

                                      -7-
<PAGE>   8

                                CITIZENS BANK OF MASSACHUSETTS

                                By:/s/ Michael St. Jean
                                   ----------------------------
                                   Title: Vice President

                                   100 Summer Street
                                   Boston, MA 02110
                                   Telecopy: (617) 338-4041

                                BANQUE NATIONALE DE PARIS

                                By:/s/ Laurent Vanderzyppe
                                   ----------------------------
                                   Title: Vice President
                                By:/s/ Marguerite L. Lebon
                                   ----------------------------
                                   Assistant Vice President

                                   499 Park Avenue, 2nd Floor
                                   New York, 10022
                                   Telecopy: (212) 415-9707

                                MELLON BANK, N.A.

                                By:/s/ John R. Cooper
                                   ----------------------------
                                   Title: Vice President

                                One Mellon Bank Center
                                Mail Code: 1510370
                                Pittsburgh, PA 15258
                                Telecopy: (412) 234-8087

                                      -8-

<PAGE>   9

                                                                     EXHIBIT 4.4

                              OFFICER'S CERTIFICATE

         Pursuant to Section 4.4 of Amendment No. 10 to Credit Agreement dated
as of December 13, 1999 (the "Amendment") among The Pioneer Group, Inc., a
Delaware corporation (the "Company"), certain of its subsidiaries signatories
thereto, the Lenders and BankBoston, N.A., f/k/a The First National Bank of
Boston, as agent (the "Agent") for itself and the other Lenders, which amends
the Credit Agreement dated as of June 6, 1996 (as amended, modified and in
effect after giving effect to the Amendment, the "Credit Agreement"), among the
Company, certain of its subsidiaries signatories thereto, the Lenders and the
Agent, the Company hereby certifies that the representations and warranties
contained in Section 3 of the Amendment are true and correct on and as of the
date hereof with the same force and effect as though originally made on and as
of the date hereof; no Default exists on the date hereof or will exist after
giving effect to the Amendment; and as of the date hereof, no Material Adverse
Change has occurred; and, as of the date hereof, the aggregate investment assets
under management by the Company and its Subsidiaries equals or exceeds
$15,000,000,000.

         Terms defined in the Credit Agreement and not otherwise defined herein
are used herein with the meanings so defined.

         This certificate has been executed by a duly authorized Executive
Officer or Financial Officer this 13th day of December, 1999.

                            THE PIONEER GROUP, INC.

                            By: /s/ Eric W. Reckard
                               ----------------------------
                                Name: Eric W. Reckard
                                Title: Executive Vice President, Chief Financial
                                       Officer and Treasurer<PAGE>   1
--------------------------------------------------------------------------------

                                                                   Exhibit 10.89

                             THE PIONEER GROUP, INC.

                            ------------------------

                          SUPPLEMENTAL AGREEMENT NO. 5

                          Dated as of November 11, 1999

                                  amending the

                   Note Agreement dated as of August 14, 1997
                                  (as amended)

                            ------------------------

                              Senior Notes due 2004

--------------------------------------------------------------------------------
<PAGE>   2
                             THE PIONEER GROUP, INC.

                          SUPPLEMENTAL AGREEMENT NO. 5

                                                         as of November 11, 1999

                            Re: Senior Notes due 2004

The Travelers Insurance Company
One Tower Square
Hartford, CT 06183-2030

Ladies and Gentlemen:

                  THE PIONEER GROUP, INC., a Delaware corporation (the
"Company"), hereby agrees with you as follows:

                  Section 1. NOTE AGREEMENT AMENDMENTS. Pursuant to the Note
Agreement dated as of August 14, 1997, as amended by Supplemental Agreement No.
1 and Supplemental Agreement No. 2, each dated as of September 30, 1998,
Supplemental Agreement No. 3, dated as of December 29, 1998 and Supplemental
Agreement No. 4, dated as of June 30, 1999 (as so amended, the "Note
Agreement"), entered into by the Company with The Travelers Insurance Company,
the Company issued and sold $20,000,000 aggregate principal amount of its Senior
Notes due 2004 (the "Notes"). Unless the context otherwise requires, capitalized
terms used herein without definition have the respective meanings ascribed
thereto in the Note Agreement. The Notes originally bore an interest rate of
7.95% per annum. Pursuant to Supplemental Agreement No. 1, such interest rate
was changed to a floating rate of interest as therein described. Pursuant to
Supplemental Agreement No. 3, such interest rate was changed to a fixed rate of
8.95% per annum. The Company has requested you, as the holder of all of the
outstanding Notes, further to amend the Note Agreement and the Notes. Subject to
this Supplemental Agreement No. 5 (this "Supplemental Agreement") becoming
effective as hereinafter provided, the Company and the holder of the Notes do
hereby agree that the Note Agreement is amended pursuant to Section 11.1 of the
Note Agreement as follows:
<PAGE>   3
                                       2

                  A.  Section 1 of the Note Agreement is amended by:

                   1. deleting the definitions of "Consolidated Tangible Net
         Worth", "Default Rate" and "Subsidiary Guarantors" in their entirety
         and replacing them with the following new definitions:

                           "'Consolidated Tangible Net Worth' means, at any
                  date, the total of:

                           (a) stockholders' equity of the Company and its
                  Subsidiaries (excluding the effect of any foreign currency
                  translation adjustments) determined in accordance with GAAP on
                  a consolidated basis, minus

                           (b) the amount by which such stockholders' equity has
                  been increased by the write-up of any asset of the Company and
                  its Subsidiaries (excluding any write-ups net of write-downs
                  associated with any venture capital investments of the Company
                  and its Subsidiaries), minus

                           (c) assets of the Company and its Subsidiaries that
                  are considered intangible assets under GAAP (including but not
                  limited to customer lists, goodwill, computer software and
                  capitalized research and development costs other than the
                  capitalized development costs relating to the natural resource
                  business operations of the Company or any of its
                  Subsidiaries), plus

                           (d) the amount by which such stockholders' equity has
                  been decreased by the after-tax noncash write-down of assets
                  employed in the Company's and its Subsidiaries' international
                  operations, up to an aggregate of all such write-downs of
                  $12,500,000."

                                     * * * *

                           "'Default Rate' means that rate of interest that is
                  the greater of (i) 11.45% and (ii) 2% above the rate of
                  interest publicly announced by Citibank, N.A. from time to
                  time at its principal office in New York City at its prime
                  rate."

                                     * * * *
<PAGE>   4
                                       3

                  B. Section 4.6 of the Note Agreement is amended by changing
the definition of "Remaining Scheduled Payments" by deleting the phrase
"determined for such purpose at the rate of 8.95%" and replacing it with the
phrase "determined for such purpose at the rate of 9.45%".

                  C. Section 7.5.3 is amended to read in its entirety as
follows:

                  "7.5.3.  Consolidated Tangible Net Worth.

                  Consolidated Tangible Net Worth shall, on and after September
         30, 1999, at all times equal or exceed $72,500,000; provided, however,
         that on the first day of each fiscal quarter of the Company beginning
         with the fiscal quarter ending September 30, 1999, such dollar amount
         shall be increased by an amount equal to 50% of the sum, for the fiscal
         quarter then most recently ended, of (i) Consolidated Net Income (only
         if in excess of zero) and (ii) the after-tax gain on the sale or
         disposition of assets or capital stock of Pioneer Goldfield Entities."

                  D. Section 7.6.1 is amended to read in its entirety as
follows:

                  "7.6.1. Indebtedness in respect of the Credit Obligations and
         the Bank Credit Facility, provided that after such Indebtedness under
         the Bank Credit Facility has been repaid in full and the Bank Credit
         Facility has been terminated, other Indebtedness of the Company
         (including without limitation in respect of the Credit Obligations)
         shall not exceed $105,000,000."

                  E. A new Section 7.9.A is hereby added to the Note Agreement
immediately after Section 7.9 to read as follows:

                  "7.9.A. Cash Expenditures.The Company and each of its
         Subsidiaries shall restrict the net amount of cash expended on
         international operations and timber operations as follows:

                  7.9.A.1. During the period commencing September 30, 1999 and
         ending March 31, 2000, the Company and its Subsidiaries shall not
         expend cash in connection with the Company's or any Subsidiary's
         international operations that in the aggregate exceeds $10,000,000, net
         of any cash provided during such period by such international
         operations.

                  7.9.A.2. During the period commencing April 1, 2000 and ending
         March 31, 2001, the Company and each of its
<PAGE>   5
                                       4

         Subsidiaries shall not expend cash in connection with the Company's or
         any Subsidiary's international operations that in the aggregate exceeds
         $15,000,000, net of any cash provided during such period by such
         international operations.

                  7.9.A.3. On and after October 1, 1999, the Company and each of
         its Subsidiaries shall not expend cash in connection with the Company's
         or any Subsidiary's timber operations that in the aggregate exceeds
         $3,000,000, net of any cash provided during such period by such timber
         operations.

                  7.9.A.4. For purposes of this Section 7.9.A, references to
         international operations shall not include any operations of the
         Company's Core Mutual Fund Subsidiaries and any Subsidiaries of such
         Core Mutual Fund Subsidiaries."

                  F. Amendment to Exhibit 2.1. Exhibit 2.1 of the Note Agreement
is deleted in its entirety and replaced with Exhibit A hereto.

                  G. Amendment to Exhibit 9.1.12. Exhibit 9.1.12 of the Note
Agreement, entitled "Officers of the Company," is deleted in its entirety and
replaced with Exhibit B hereto.

                  Section 2. AMENDMENT OF OUTSTANDING NOTE. Subject to this
Supplemental Agreement becoming effective, the text of the outstanding Note
(other than the date, the name of the payee and the principal amount, which are
unchanged), is amended pursuant to Section 11.1 of the Note Agreement, to read
as provided in Exhibit A to this Supplemental Agreement.

                  Section 3. REPRESENTATIONS AND WARRANTIES OF THE COMPANY. The
Company represents and warrants to you as follows:

                 A. Organization, Authorization, Etc. The Company and each of
its Subsidiaries is a corporation duly organized, validly existing and in good
standing under the laws of the State of its organization, and has all requisite
power and authority to execute, deliver and perform its obligations under the
Note Agreement as amended by this Supplemental Agreement.

         The execution, delivery and performance of this Supplemental Agreement
has been duly authorized by all necessary corporate and, if required,
stockholder action on the part of the Company and each Subsidiary Guarantor, as
applicable. This Supplemental Agreement is a legal, valid and binding obligation
of the Company and the Subsidiary Guarantors, as applicable, enforceable against
the Company or such Subsidiary Guarantors in accordance with its terms, except
as enforceability may be limited by bankruptcy,
<PAGE>   6
                                       5

insolvency, reorganization, fraudulent transfer, moratorium or other similar
laws relating to or affecting creditors' rights generally and by general
principles of equity (regardless of whether such enforceability is considered in
a proceeding in equity or at law).

                 B. Compliance with Laws, Other Instruments, Etc. The execution,
delivery and performance by the Company or the Subsidiary Guarantors of this
Supplemental Agreement does not and will not (A) contravene, result in any
breach of, or constitute a default under, or result in the creation of any Lien
in respect of any property of the Company or any Subsidiary under any indenture,
mortgage, deed of trust, loan, purchase or credit agreement, lease, corporate
charter or by-laws, or any other agreement or instrument to which the Company or
any Subsidiary is bound or by which the Company or any Subsidiary or any of
their respective properties may be bound or affected, (B) conflict with or
result in a breach of any of the terms, conditions or provisions of any order,
judgment, decree, or ruling of any court, arbitrator or Governmental Authority
applicable to the Company or any Subsidiary or (C) violate any provision of any
statute or other rule or regulation of any Governmental Authority applicable to
the Company or any Subsidiary.

                 C. Governmental Authorizations, Etc. No consent, approval or
authorization of, or registration, filing or declaration with, any Governmental
Authority is required in connection with the execution, delivery or performance
by the Company or any Subsidiary Guarantor of this Supplemental Agreement.

                 D. No Default, etc. No Event of Default or Default has occurred
and is continuing, and neither the Company nor any Core Mutual Fund Subsidiary
is in default (whether or not waived) in the performance or observance of any of
the terms, covenants or conditions contained in any instrument evidencing any
Indebtedness and there is no pending request by the Company (except pursuant to
this Supplemental Agreement) or any such Subsidiary for any amendment or waiver
in respect of any contemplated or possible default with respect to such
Indebtedness and no event has occurred and is continuing which, with notice or
lapse of time or both, would become such a default.

                 E. No Undisclosed Fees. The Company has not, directly or
indirectly, other than with respect to the payment of consideration disclosed to
the Noteholders, paid or caused to be paid any consideration (as supplemental or
additional interest, a fee or otherwise) to any party to the Bank Credit
Facility in order to induce such party to enter into an agreement
<PAGE>   7
                                       6

substantially similar to this Supplemental Agreement, nor has the Company agreed
to made any such payment.

                  Section 4. REPRESENTATION OF THE NOTEHOLDER. You represent to
the Company that you are the beneficial owner of Notes in an aggregate principal
amount of $20,000,000.

                  Section 5. EFFECTIVENESS OF THIS SUPPLEMENTAL AGREEMENT. This
Supplemental Agreement shall become effective on the date (the "Effective Date")
on which all of the following conditions precedent shall have been satisfied:

                 A. Proceedings. All proceedings taken by the Company and the
Subsidiary Guarantors in connection with the transactions contemplated hereby
and all documents and papers incident thereto shall be satisfactory to you, and
you and your special counsel shall have received all such counterpart originals
or certified or other copies of such documents and papers, all in form and
substance satisfactory to you, as you or they may reasonably request in
connection therewith.

                 B. Representations and Warranties. The representations and
warranties of the Company contained in Section 3 of this Supplemental Agreement
shall be true on and as of the Effective Date as though such representations and
warranties had been made on and as of the Effective Date, and you shall have
received a certificate of a senior financial officer of the Company, dated the
Effective Date, to such effect.

                 C. Opinion of Counsel for the Company. You shall have received
an opinion in form and substance satisfactory to you, dated the date of this
Supplemental Agreement, from Robert P. Nault, General Counsel for the Company,
concerning the due authorization, execution, delivery and performance of this
Supplemental Agreement and such other matters incident to the transactions
contemplated hereby as you may reasonably request.

                  D. Cash Flow Forecasts. The Company shall have provided
monthly cash flow forecasts for the period commencing October 1, 1999 and ending
June 30, 2000.
                  E. Payment of Fees. The Company shall have paid you an
amendment fee equal to 0.50% of the unpaid principal amount of the Notes and an
administrative fee of $36,000. The Company shall have also paid the fees and
disbursements of your special counsel as contemplated by Section 8 of this
Supplemental Agreement.

                 Section 6. CONDITION SUBSEQUENT. You agree to release Pioneer
Management (Ireland) Limited from the Guarantee subject
<PAGE>   8
                                       7

to the condition subsequent that the Company shall have obtained from the
lenders party to the Bank Credit Facility within thirty days of the Effective
Date, as defined herein, documentation sufficient to release Pioneer Management
(Ireland) Limited as guarantor under the Bank Credit Facility. You agree that
this release is effective as of January 1, 1999.

                  Section 7. EXCHANGE OR NOTATION OF NOTES. Prior to any
transfer of an outstanding Note you agree that you will either make a notation
of the amendment of such Note pursuant to this Supplemental Agreement, or
surrender such Note in exchange for a new Note in accordance with Section 12.2
of the Note Agreement. Any Note executed and delivered on or after the Effective
Date shall be in the form of Exhibit A hereto.

                  Section 8. EXPENSES. Without limiting the generality of
Section 5.8 of the Note Agreement, the Company agrees, whether or not the
transactions contemplated hereby are consummated, to pay the reasonable fees and
disbursements and other charges of Willkie Farr & Gallagher, your special
counsel, for their services rendered in connection with such transactions and
with respect to this Supplemental Agreement and any other document delivered
pursuant to this Supplemental Agreement and reimburse you for your out-of-pocket
expenses in connection with the foregoing.
<PAGE>   9
                                       8

                  Section 9. RATIFICATION. Except as amended hereby, the Note
Agreement is in all respects ratified and confirmed and the provisions thereof
shall remain in full force and effect, and the Subsidiary Guarantors hereby
ratify their obligations thereunder and under the Subsidiary Guarantees to which
they are a party.

                  Section 10. COUNTERPARTS. This Supplemental Agreement may be
executed in two or more counterparts, each of which shall be deemed an original,
but all of which together shall constitute one and the same instrument.

                  Section 11. GOVERNING LAW. This Supplemental Agreement shall
be governed by and construed in accordance with the laws of the State of New
York.

                  If you are in agreement with the foregoing, please sign the
form of acceptance in the space below provided, whereupon this Supplemental
Agreement shall become a binding agreement between you and the Company, with the
approval of the Subsidiary Guarantors, subject to becoming effective as
hereinabove provided.

                                      THE PIONEER GROUP, INC.

                                      By:/s/ Eric W. Reckard
                                         ----------------------------------
                                         Title: Executive Vice President,
                                               Chief Financial Officer and
                                               Treasurer

                                      60 State Street
                                      Boston, MA 02109-1820

                                      SUBSIDIARY GUARANTORS

                                      PIONEER INVESTMENT MANAGEMENT, INC.

                                      By:/s/ Eric W. Reckard
                                         ----------------------------------
                                         Title: Treasurer

                                      60 State Street
                                      Boston, MA 02109-1820

                                      PIONEER MANAGEMENT (IRELAND) LTD.

                                      By:/s/ John F. Cogan, Jr.
                                         ----------------------------------
                                         Title: Director

                                      60 State Street
                                      Boston, MA 02109-1820
<PAGE>   10
                                       9

                                      PIONEERING SERVICES CORPORATION

                                      By:/s/ Eric W. Reckard
                                         ----------------------------------
                                         Title: Treasurer

                                      60 State Street
                                      Boston, MA 02109-1820

  ACCEPTED

  THE TRAVELERS INSURANCE COMPANY

  By: /s/ Pamela Westmoreland
     -------------------------
     Title: Investment Officer
<PAGE>   11
                                    EXHIBIT A

                                                                     EXHIBIT 2.1

                                 [FORM OF NOTE]

                             THE PIONEER GROUP, INC.

                           9.45% Senior Note due 2004

No. R-                                                       New York, New York
$______________                                                          [Date]
PPN:[ ]

                  THE PIONEER GROUP, INC., a Delaware corporation (the
"Company"), for value received, hereby promises to pay to ____________________,
or registered assigns, the principal sum of ____________________ Dollars (or so
much thereof as shall not have been prepaid) on August 15, 2004, and to pay
interest (computed on the basis of a 360-day year of twelve 30-day months) on
the unpaid principal balance thereof from the date of this Note at the rate of
9.45% per annum, quarterly on February 15, May 15, August 15 and November 15 in
each year until such principal sum shall have become due and payable (whether at
maturity, at a date fixed for prepayment or by declaration, acceleration or
otherwise), and to pay on demand interest (so computed) on any overdue principal
and premium, if any, and (to the extent permitted by applicable law) on any
overdue interest, at a rate per annum equal to the greater (determined on a
daily basis) of (i) 11.45% and (ii) 2% above the rate of interest publicly
announced by Citibank, N.A. from time to time at its principal office in The
City of New York as its prime or base rate. Payments of principal, premium, if
any, and interest shall be made in such coin or currency of the United States of
America as at the time of payment is legal tender for the payment of public and
private debts in the manner and to the address designated by the holder hereof
and, in the absence of such designation, at said principal office of Citibank,
N.A.

                  This Note is one of an issue of Senior Notes of the Company
issued pursuant to the Note Agreement dated as of August 14, 1997, as amended by
Supplemental Agreement No. 1 dated as of September 30, 1998, Supplemental
Agreement No. 2 dated as of September 30, 1998, Supplemental Agreement No. 3
dated as of December 30, 1998, Supplemental Agreement No. 4 dated as of June 30,
1999 and Supplemental Agreement No. 5 dated as of November 11, 1999 (as so
amended, the "Note Agreement"), entered into by the Company and certain of its
Subsidiaries, as guarantors, with an institutional investor. The holder of this
Note is entitled to the
<PAGE>   12
benefits of the Note Agreement and is also entitled to the benefits of a certain
Intercreditor Agreement referred to therein.

                  The Company may at its election prepay this Note, in whole or
in part, and the maturity hereof may be accelerated following an Event of
Default, all as provided in the Note Agreement, to which reference is made for
the terms and conditions of such provisions as to prepayment and acceleration,
including without limitation the payment of a make-whole premium in connection
therewith.

                  Upon surrender of this Note for registration of transfer or
exchange, duly endorsed or accompanied by a written instrument of transfer duly
executed by the registered holder hereof or such holder's attorney duly
authorized in writing, a new Note for a like principal amount will be issued to,
and, at the option of the holder, registered in the name of, the transferee. The
Company and any agent of the Company may deem and treat the person in whose name
this Note is registered as the owner hereof for the purpose of receiving
payments of the principal of, premium, if any, and interest hereon and for all
other purposes whatsoever, whether or not this Note is overdue, and the Company
shall not be affected by any notice to the contrary.

                  As provided in the Note Agreement, this Note shall be governed
by and construed in accordance with the law of the State of New York.

                                   THE PIONEER GROUP, INC.

                                   By_______________________________
                                     Title:
<PAGE>   13
                                    EXHIBIT B

                                 Exhibit 9.1.12

                             OFFICERS OF THE COMPANY

1.  John F. Cogan, Jr.     Chairman of the Board, Chief Executive Officer and
                           President of the Company
2.  Eric W. Reckard        Executive Vice President, Chief Financial Officer and
                           Treasurer of the Company and Subsidiaries
3.  David D. Tripple       Executive Vice President of the Company and President
                           of Pioneer Investment Management, Inc. and Pioneer
                           Funds Distributor, Inc.
4.  William H. Smith, Jr.  Executive Vice President of the Company and Director
                           of Pioneering Services Corporation
5.  Roger K. Leonard       Managing Director and Chief Executive of Pioneer
                           Goldfields Limited and Managing Director of Teberebie
                           Goldfields Limited

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