<PAGE>   1
                       SECURITIES AND EXCHANGE COMMISSION
                              Washington, DC 20549

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

                                  FORM 10-K/A
                               (Amendment No. 1)


[X]      ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES
         EXCHANGE ACT OF 1934

For the Fiscal Year ended December 31, 1999
Commission File Number 0-27393

                        CUMBERLAND BANCORP, INCORPORATED
             (Exact name of registrant as specified in its charter)

<TABLE>
         <S>                                          <C>
                       Tennessee                                  62 - 1297760
         -----------------------------------------    ------------------------------------
         (State or other jurisdiction                 (I.R.S. Employer Identification No.)
         of incorporation or organization)

         4205 Hillsboro Road,
         Nashville, Tennessee                                         37215
         -----------------------------------------    ------------------------------------
         (Address of principal executive offices)                    (Zip Code)
</TABLE>

Registrant's telephone number, including area code:
(615) 377-9395

Securities registered pursuant to Section 12(b) of the Act:
None

Securities registered pursuant to Section 12(g) of the Act:
None

                     Common Stock, $.50 par value per share
      --------------------------------------------------------------------
                                (Title of Class)

Indicate by check mark whether the registrant: (1) has filed all reports
required to be filed by Section 13 or 15(d) of the Exchange Act of 1934 during
the preceding 12 months (or for such shorter period that the registrant was
required to file such reports), and (2) has been subject to such filing
requirements for the past 90 days.

                                               YES [X]       NO [ ]

Indicate by check mark if disclosure of delinquent filers pursuant to Item 405
of Regulation S-K is not contained herein and will not be contained, to the best
of the registrant's knowledge, in definitive proxy or information statements
incorporated by reference in Part III of this Form 10-K or any amendment to this
Form 10-K.   [ ]

The aggregate market value of the voting stock held by non-affiliates of the
registrant on February 29, 2000, was approximately $38,188,044. The market value
calculation was determined using $12.50 per share.

Shares of common stock, $0.50 par value per share, outstanding on February 29,
2000 were 6,863,724

                      DOCUMENTS INCORPORATED BY REFERENCE

<TABLE>
<CAPTION>

Part of Form 10-K          Documents from which portions are incorporated by reference
-----------------          ------------------------------------------------------------
<S>                        <C>
Part III                   Portions of the Registrant's definitive proxy statement,
                           relating to the Registrant's Annual Meeting of Shareholders
                           to be held on April 27, 2000 are incorporated by
                           reference into Items 10, 11, 12 and 13.
</TABLE>


<PAGE>   2

ITEM 7. MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS
OF OPERATIONS

                        CAUTIONARY STATEMENT CONCERNING
                          FORWARD-LOOKING INFORMATION

         This section along with other sections in this document, contains or
incorporates by reference certain "forward-looking statements" within the
meaning of Section 27A of the Securities Act of 1933, as amended (the
"Securities Act"), and Section 21E of the Securities Exchange Act of 1934, as
amended (the "Exchange Act"), which are intended to be covered by the "safe
harbors" created thereby. Those statements include, but may not be limited to,
the discussions of the Company's expectations concerning its future
profitability, operating performance, growth strategy and its assumptions
regarding other matters. Also, when any of the words "believes", "expects",
"anticipates", "intends", "estimates", "plans", or similar terms or expressions,
are used in this document, forward-looking statements are being made.

         You should be aware that, while the Company believes the expectations
reflected in those forward-looking statements are reasonable, they are
inherently subject to risks and uncertainties which could cause the Company's
future results and stockholder values to differ materially from the Company's
expectations. These factors are disclosed in this section. Because of these
factors, there can be no assurance that the forward-looking statements included
or incorporated by reference herein will prove to be accurate. In light of the
significant uncertainties inherent in the forward-looking statements included or
incorporated by reference herein, you should not regard the inclusion of such
information as a representation by the Company or any other person that the
objectives and plans of the Company will be achieved. In addition, the Company
does not intend to, and is not obligated to, update these forward-looking
statements after the date hereof, even if new information, future events or
other circumstances have made them incorrect or misleading as of any future
date.

         You should read the following discussion in conjunction with our
financial statements and the notes to those statements appearing elsewhere in
this document.

                                      13
<PAGE>   3

         Cumberland Bancorp, Incorporated had several significant events that
occurred during 1999 which affected its financial condition and results of
operations. An initial public offering was completed in the last half of the
year which raised approximately $8.5 million in net additional capital.
Bancshares of Dyer, Inc. (a one bank holding company with total assets of
approximately $40 million at December 31, 1999) was acquired in late December
1999. This transaction was accounted for as a pooling of interest and prior
period amounts have been restated to include the accounts and results of
operations of Dyer. Two branches totaling $20 million were acquired from another
financial institution and investments in unconsolidated subsidiaries were made
of approximately $2 million.

         Financial Condition. Our total assets grew from $408.7 million at
year-end 1998 to $525.5 million at December 31, 1999, a $116.8 million increase
or 29%. The primary changes in assets were related to the $117 million increase
in net loans. In addition, cash and due from banks increased $9.2 million to
allow for possible cash needs related to uncertainties about the Year 2000
issue. We funded these increases primarily by an increase in deposits of $78
million and by decreasing our interest-bearing deposits held in other
institutions by $16.6 million.

         Our total liabilities grew from $387 million at year end 1998 to $490
million at December 31, 1999, a $104 million increase or 27%. In addition to
the deposit growth mentioned above, federal funds purchased increased $2.2
million and advances from the Federal Home Loan Bank increased $21.6 million.

         Stockholders' equity increased $13.2 million to $35.3 million at
December 31, 1999. The increase is related to the previously mentioned IPO, and
privately placed common stock of approximately $2 million. Retained earnings
provide the balance of the increase in equity. Our leverage capital ratio
increased from 5.45% at December 31, 1998 to 6.84% at December 31, 1999. See
note 14 to our consolidated financial statements for more information relating
to capital.

RESULTS OF OPERATIONS YEAR ENDED DECEMBER 31, 1999 COMPARED TO THE YEAR ENDED
DECEMBER 31, 1998

         Net earnings were $3.5 million in 1999 compared to $3.3 million in
1998. Total revenues increased 16% while total expenses increased 18% during
1999 as compared to the prior year. As discussed in more detail later, our
portion of the operating loss of the investment in The Murray Bank, merger and
acquisition expenses relating to Bancshares of Dyer, Inc. and start up costs
associated with other market expansions negatively affected earnings in 1999.

         Net interest income increased $4.2 million, or 26%, to $20.1 million
in 1999 from $17.4 million in 1998. The increase is a result of growth in
average earning assets of our Cumberland Bank subsidiary throughout the year,
and our BankTennessee and Community Bank subsidiaries for the last six months.

         The Company's net interest spread and net yield on earning assets were
4.66% and 4.71% respectively, in 1999 as compared to 4.41% and 4.50% in 1998.
The increase in net interest spread and net yield on earning assets was the
result of yields on earning assets increasing faster than rates paid on
interest bearing liabilities. Net interest spread represents the difference in
the yield on earning assets and the rate paid on interest bearing liabilities.
Net yield on earning assets is net interest income divided by average earning
assets.

         The provision for loan losses was $1.6 million in 1999 compared to
$1.2 million in 1998, a 37% increase. The increase in the provision was
primarily attributable to the 36.3% increase in loans.

         Noninterest income increased $120,000, or 3%, to $4.4 million in 1999
from $4.3 million in 1998. Mortgage banking income declined $443,000 or 32%
from 1998 levels, primarily due to reduction in activity related to rising
interest rates.


                                      14
<PAGE>   4
         Noninterest expense increased $3.6 million, or 26%, to $17.2 million in
1999 from $13.6 million in 1998. Included in noninterest expense is
approximately $116,000 in 1999 related to losses of unconsolidated subsidiaries,
compared to $92,000 in the prior year. Also included in 1999 are expenses
related to the organization of new entities and to expenses associated with our
mergers and acquisitions of approximately $102,000 (See Note 17 to our Notes to
Consolidated Financial Statements for more information regarding these
activities). Other increases in other expenses are primarily a result of overall
growth. Salaries and benefits increased from $7.1 million in 1998 to $9.2
million in 1999 or an increase of 29%.

YEAR ENDED DECEMBER 31, 1998 COMPARED TO THE YEAR ENDED DECEMBER 31, 1997

         The comparison of 1998 to 1997 operating results is substantially
affected by our merger with First Federal, which occurred on July 1, 1997.
Total assets and operating results for The Community Bank and BankTennessee in
1997 are only included in the second six months of the Results of Operations.

         Net interest income increased $5.9 million, or 58%, to $15.9 million
in 1998 from $10.1 million in 1997. Of this increase, $2.8 million, or 47%, is
attributable to the addition of First Federal's assets and liabilities in
mid-year 1997. The remaining $3.1 million, or 53%, increase is a result of
growth in average earning assets of our Cumberland Bank subsidiary throughout
the year, and our BankTennessee and Community Bank subsidiaries for the last
six months.

         The Company's net interest spread and net yield on earning assets were
4.41% and 4.50% respectively, in 1998 as compared to 4.57% and 4.69% in 1997.
The decrease in net interest spread and net yield on earning assets was the
result of yields on earning assets declining faster than rates paid on interest
bearing liabilities. Net interest spread represents the difference in the yield
on earning assets and the rate paid on interest bearing liabilities. Net yield
on earning assets is net interest income divided by average earning assets.

         The provision for loan losses was $1.2 million in 1998 compared to
$1.4 million in 1997. The decrease in the provision was primarily attributable
to lower charge-offs in 1998, partially offset by an increase in loan volume
due to growth and our merger with First Federal.

         Noninterest income increased $870,000, or 26%, to $4.3 million in 1998
from $3.4 million in 1997. Noninterest income of First Federal for the first
sixth months of 1997 (prior to the merger) was $413,000. After adjusting for
the $550,000 gain on the sale of a branch that was recognized during the last
half of 1997, noninterest income increased $1.5 million, or 44%. In addition to
the effect of a full year of noninterest income from BankTennessee and The
Community Bank, noninterest income also increased because of improved mortgage
banking operations due to market conditions and gains on sales of SBA loans.

         Noninterest expense increased $4.9 million, or 57%, to $13.6 million
in 1998 from $8.7 million in 1997. Of the increase, $2.6 million, or 53%, is
related to the effect of BankTennessee's and The Community Bank's operations in
1998. The remaining $2.3 million increase, or 47%, is a result of our overall
growth. Salaries and benefits increased from $4.4 million in 1997 to $7.1
million in 1998 or an increase of 63%. The increase is due to the large
increase in total employees who work for BankTennessee and The Community Bank.
Our efficiency ratio in 1998 was 67.5%, compared to 64.1% in 1997.

         Net income increased $1.2 million or 57%, to $3.3 million in 1998. Of
this increase, $400,000 is due to the effects of the merger with First Federal.
Return on average assets during 1998 and 1997 was 0.89% and 0.95% respectively,
and return on average equity was 16.63% in 1998 compared to 16.57% for 1997.


                                      15
<PAGE>   5
LOANS

     The following table presents various categories of loans contained in our
banks' loan portfolio for the periods indicated and the total amount of all
loans for such period:

<TABLE>
<CAPTION>

                                                                DECEMBER 31,

                                      1999           1998           1997           1996          1995
                                      ----           ----           ----           ----          ----
                                                              (In thousands)
<S>                               <C>              <C>            <C>            <C>            <C>
TYPE OF LOAN
------------
Real estate-construction and
     development                  $  80,789         55,220         42,819          7,573         4,852
Real estate-1 to 4 family
     residential                    157,820        140,138        121,928         43,143        29,709
Real estate other                    49,708         12,555         26,956          5,923        11,441
Commercial, financial and
agricultural                        102,385         71,070         38,977         18,762        12,292
Consumer                             50,643         45,431         41,941         32,083        27,517
Other                                 1,744            746            208            193           397
                                  ---------        -------        -------        -------        ------
Total loans                         443,089        325,160        272,829        107,677        86,208
Unearned income and
deferred
fees                                 (2,773)        (3,613)        (3,451)        (2,536)       (2,649)
                                  ---------        -------        -------        -------        ------
     Net loans                    $ 440,316        321,547        269,378        105,141        83,559
                                  =========        =======        =======        =======        ======
</TABLE>

     Loan growth was $118 million, or 36.3%, during 1999, and $52.3 million, or
19.2%, during 1998. Of this increase, $13.5 million, or 11.4% was through
acquisition of the McMinnville branches. We believe that the remaining loan
growth reported in 1999 approximates the normal trend for our four operating
bank subsidiaries. Loans continued to grow during 1999 as a result of strong
economic conditions in our banks' primary markets, with commercial loans
experiencing the largest growth. We believe that commercial loans and loans to
the residential real estate industry will continue to be our two primary loan
categories.

     At December 31, 1999, 1-4 family residential real estate loans constituted
36% of total loans and construction and development loans constituted 18% of
total loans. Construction and development loans typically involve 1-4 family
residential properties or loans to develop subdivisions of such properties. More
than half of our construction and development loans are made to finance
speculative construction by builders. The remaining builder loans are for
custom-built homes or where there are already contracts for sale. Most of our
real estate loans are secured by properties located in the primary service areas
of our banks.

     The following is a presentation of an analysis of maturities of loans as of
December 31, 1999:

<TABLE>
<CAPTION>

                                           DUE IN 1    DUE IN 1 TO  DUE AFTER 5
                 TYPE OF LOAN            YEAR OR LESS    5 YEARS      YEARS       TOTAL
                                                            (In thousands)
<S>                                      <C>           <C>          <C>          <C>
Real estate-construction & development       79,173        1,561          55       80,789
Real estate-1-4 family residential           91,536       55,237      11,047      157,820
Real estate-other                            29,825       19,300         583       49,708
Commercial, financial and agricultural       47,431       52,815       2,139      102,385
Consumer                                     27,854       20,103       2,686       50,643
Other                                         1,424          320           0        1,744
     Total                                  277,243      149,336      16,510      443,089
</TABLE>

     At December 31, 1999, $155.6 million in loans due after one year had
predetermined interest rates and $10.2 million in loans due after one year had
floating interest rates.

     It is our philosophy to pursue real estate lending as our core type of
lending relationship. Of our combined loan portfolio, 53.9% is secured by
residential real estate. Management believes this type of


                                      16
<PAGE>   6


lending has allowed us to maintain low levels of charge-offs and non-performing
loans. However, the real estate lending market has traditionally been sensitive
to interest rates, and the volume of such loans may decline if interest rates
continue to increase.

PROVISION FOR LOAN LOSSES AND ASSET QUALITY

     The provision for loan losses represents charges made to earnings to
maintain an adequate allowance for loan losses. The allowance is maintained at
an amount believed to be sufficient to absorb losses in the loan portfolio.
Factors considered in establishing an appropriate allowance include a careful
assessment of the financial condition of the borrower; a realistic determination
of the value and adequacy of underlying collateral; the condition of the local
economy and the condition of the specific industry of the borrower; a
comprehensive analysis of the levels and trends of loan categories; and a review
of delinquent and classified loans. We apply a systematic process for
determining the adequacy of the allowance for loan losses, including an internal
loan review function and a monthly analysis of the adequacy of the allowance.
Our monthly analysis includes determination of specific potential loss factors
on individual classified loans, historical potential loss factors derived from
actual net charge-off experience and trends in nonperforming loans, and
potential loss factors for other loan portfolio risks such as loan
concentrations, local economy, and the nature and volume of loans.

     An analysis of our loss experience, as well as a breakdown of the allowance
for possible loan losses, is furnished in the following table for the periods
indicated:

<TABLE>
<CAPTION>

                                                                            YEARS ENDED DECEMBER 31,
                                                               1999          1998          1997          1996          1995
                                                               ----          ----          ----          ----          ----
                                                                             (Dollars in thousands)
<S>                                                        <C>             <C>           <C>           <C>           <C>
Balance at beginning of year                               $   4,012         3,214         1,386         1,255          947
Allowance increases due to acquisitions                          152            --         1,229            --           --
                                                           ---------      --------      --------      --------      -------
Loans charged-off:
     Real estate-construction & development                       --           (65)           --            --           --
     Real estate-1 to 4 single family                           (117)          (45)          (23)           (5)
     Real estate-other                                            --            --           (90)           --           --
     Commercial, financial & agricultural                       (123)          (54)          (35)           (1)          --
     Consumer                                                   (518)         (324)         (721)         (336)        (107)
     Other                                                        --           (24)           --            --           --
                                                           ---------      --------      --------      --------      -------
         Total charge-offs                                      (758)         (512)         (869)         (342)        (107)
                                                           ---------      --------      --------      --------      -------

Charge-offs recovered:
     Real estate - construction & development                     --            21            --            --           --
     Real estate - 1-4 single family                               9             2            11            --           --
     Real estate - other                                          --             0            --            --           --
     Commercial                                                   19             5             1             4           --
     Consumer                                                     89            76            66            39           45
     Other                                                        --            18            --            --           --
                                                           ---------      --------      --------      --------      -------
         Total recoveries                                        117           122            78            43           45
                                                           ---------      --------      --------      --------      -------

Net loans charged-off                                           (641)         (390)         (791)         (299)         (62)
Current year provision                                         1,623         1,188         1,390           430          370
                                                           ---------      --------      --------      --------      -------
Balance at end of year                                     $   5,146         4,012         3,214         1,386        1,255
                                                           =========      ========      ========      ========      =======

Loans at year end                                            440,316       321,547       269,378       105,141       83,559
Ratio of allowance to loans at year end                         1.17%         1.25%         1.19%         1.32%        1.50%
Average loans                                                374,716       293,665       184,792        98,036       77,526
Ratio of net loans charged off to average loans                 0.17%         0.13%         0.43%         0.31%        0.08%
</TABLE>

     The recorded values of loans actually removed from the consolidated balance
sheets are referred to as charge-offs and, after netting out recoveries on
previously charged-off assets, become net charge-offs. Our policy is to charge
off loans, when, in management's opinion, the loan is deemed uncollectible,
although


                                      17
<PAGE>   7


concerted efforts are made to maximize recovery. Our level of net charge-offs to
average loans was 0.17% in 1999 and 0.13% in 1998. Charge-offs were higher due
to consumer loan losses for Cumberland Bank and Cumberland Finance, its finance
company subsidiary, in 1999. During 1999, the provision for loan losses of $1.6
million was almost $400,000 more than the preceding year. Factors which gave
rise to the increased provision in 1999 were the $117 million loan growth our
institutions sustained and the $194,000 increase in consumer loan losses in
Cumberland Bank's portfolio and similar loan losses in Cumberland Finance.

     The level of non-performing loans is an important element in assessing
asset quality and the relevant risk in the credit portfolio. Non-performing
loans include non-accrual loans, restructured loans and loans delinquent 90 days
or more. Loans are classified as non-accrual when management believes that
collection of interest is doubtful. When loans are placed on nonaccrual status,
all unpaid accrued interest is reversed. Another element associated with asset
quality is foreclosed properties, which represent real estate or personal
property acquired through loan defaults by customers.

     The following table presents information regarding nonaccrual, past due and
restructured loans, and foreclosed properties at the dates indicated:

<TABLE>
<CAPTION>

                                                    DECEMBER 31,

                                      1999     1998      1997   1996    1995
                                      ----     ----      ----   ----    ----
                                               (Dollars in Thousands)
<S>                                  <C>       <C>      <C>      <C>    <C>
Loans accounted for on a non-
accrual basis                        $2,446    1,745    1,561    565      489

Accruing loans which are
contractually past due 90 days or
more as to principal and interest
payments                                241      467       86    428      554

Restructured loans                      693      652      443     --       --
                                     ------    -----    -----    ---    -----
Total nonperforming loans (1)         3,380    2,864    2,090    993    1,043

Foreclosed properties                $2,400      610      630    502      630
</TABLE>

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

 (1) As of December 31, 1999, all restructured loans were in compliance with
their modified terms.

     Non-performing loans were 0.8% and 0.9% of loans at December 31, 1999 and
1998, respectively. The dollar increase in non-performing loans during 1999 is
due to a growing and maturing portfolio, and less attributable to conditions in
the marketplace. Additional interest income of approximately $125,000 in 1999,
$121,000 in 1998, $79,000 in 1997, $33,000 in 1996, and $26,000 in 1995 would
have been recorded if all loans accounted for on a non-accrual basis had been
current in accordance with their original terms. No interest income has been
recognized during the five year period ended December 31, 1999 on loans that
have been accounted for on a non-accrual basis.

         Management has internally classified approximately $4.3 million in
loans as "substandard" based upon other possible credit problems. These loans
are not included in the above amounts. These loans are performing loans but are
classified as "substandard" due to payment history, decline in the borrowers
financial position or decline in collateral value. Loans classified as
"substandard" are inadequately protected by the current sound worth and paying
capacity of the obligor or the collateral pledged, if any. Loans so


                                       18
<PAGE>   8


classified must have a well-defined weakness or weakness that jeopardize the
liquidation of the debt. Loans classified as "doubtful" have all the weaknesses
inherent in one classified "substandard", with the added characteristic that the
weaknesses make collection or liquidation in full, on the basis of currently
existing facts, conditions and values, highly questionable and improbable. Loans
classified as "loss" are considered uncollectible and of such little value that
their continuance as bankable assets is not warranted.

     As of December 31, 1999, there are no loans classified by our regulators or
management as loss, doubtful or substandard that have not been disclosed above
or which represent or result from trends or uncertainties which management
reasonably expects will materially impact future operating results, liquidity,
or capital resources, or represent material credits about which management is
aware of any information which causes management to have serious doubts as to
the ability of such borrowers to comply with the loan repayment terms.

     The allocation of the allowance for loan losses by loan category at
December 31, of the years indicated is presented below:

<TABLE>
<CAPTION>

                                                                 AS OF DECEMBER 31,
                    ---------------------------------------------------------------------------------------------------
                                 1999                               1998                          1997
                                 ----                               ----                          ----
                                            PERCENT OF                       PERCENT OF                      PERCENT OF
                                            LOANS IN                         LOANS IN                        LOANS IN
                                              EACH                             EACH                           EACH
                               PERCENT OF   CATEGORY             PERCENT OF  CATEGORY            PERCENT OF  CATEGORY
                               ALLOWANCE    TO TOTAL             ALLOWANCE   TO TOTAL            ALLOWANCE   TO TOTAL
                               TO TOTAL        -----             TO TOTAL       -----            TO TOTAL      -----
                     AMOUNT    ALLOWANCE     LOANS     AMOUNT    ALLOWANCE    LOANS     AMOUNT   ALLOWANCE    LOAN
                     ------    ---------     -----     ------    ---------    -----     ------   ---------    ----
<S>                  <C>       <C>          <C>        <C>       <C>         <C>       <C>         <C>         <C>
Real estate -
construction &
 development.....    $1,029       20%         18%        802        20%        18%       643        20%         16%
Real estate-1-4
single family....       257        5%         36%        201         5%        42%       161         5%         44%
Real estate - other     309        6%         11%        160         4%         4%       129         4%         11%
Commercial,
   financial and
   agriculture...     1,132       22%         23%        883        22%        23%       482        15%         14%
Consumer.........     1,647       32%         11%      1,204        30%        12%       804        25%         14%
Other............       103        2%          1%         80         2%         1%        64         2%          1%
Unallocated......       669       13%                    682         17%                 931         29%
                     ------      ---         ---       -----       ---        ---      -----       ---         ---
       Total         $5,146      100%        100%      4,012       100%       100%     3,214       100%        100%
                     ======      ===         ===       =====       ===        ===      =====       ===         ===
</TABLE>


     As of December 31, 1999, real estate mortgage loans constituted 65% of
outstanding loans. Approximately $126 million, or 44%, of this category
represents first mortgage residential real estate mortgages where the amount of
the original loan generally does not exceed 80% of the appraised value of the
collateral. We have $80.8 million in construction and development loans, which
are primarily related to the home building industry in Shelby, Williamson,
Davidson and Sumner Counties, Tennessee. The remaining portion of this category
consists primarily of commercial real estate loans. Risk of loss for these loans
is generally higher than residential loans. Therefore, management has allocated
a significant portion of the allowance for loan losses to this category.

SECURITIES

     Our banks' securities portfolios are primarily used as a source of
liquidity. Total securities were $22.9 million at year-end 1999, which is down
$3.8 million from year-end 1998. The securities portfolios comprised 4.4% of
total assets at year-end 1999. Our banks' policy guidelines are designed to
minimize credit, market and liquidity risk. Securities generally must be
"investment grade" or higher to be purchased. Over the last year, a majority of
newly-purchased securities have been designated as "Available for Sale" to
increase flexibility for asset liability management. Approximately 42% of
securities held at year-end 1999


                                       19
<PAGE>   9


were pledged for public deposits. Other than commitments to originate or sell
mortgage loans, our banks do not invest in off-balance sheet derivative
financial instruments.

     We invest primarily in obligations of the United States or obligations
guaranteed as to principal and interest by the United States, other taxable
securities and in certain obligations of states and municipalities. The majority
of the mortgage-backed securities are instruments of U.S. Government agencies.
In addition, we enter into federal funds transactions with our principal
correspondent banks, and act as a net seller of such funds. We did not hold
securities of any single issuer that exceeded ten percent of shareholders'
equity.

     The following tables present, for the periods indicated, the carrying
amount of our securities portfolio, including mortgage-backed securities,
segregated into available for sale and those held to maturity categories.

<TABLE>
<CAPTION>

                                              At December 31,

                                       1999        1998         1997
                                          (Dollars in thousands)
<S>                                  <C>          <C>          <C>
Available for sale:
   U.S. Government and agencies      $10,378      10,471       1,602
   Obligations of SCM                  2,727       1,844       1,397
   Mortgage-backed                     1,464       3,384       1,409
   Other debt securities                 262          --         676
   Marketable equity securities        1,382       1,571       1,445
                                     -------      ------      ------

      Total available for sale        16,213      17,270       6,529
                                     -------      ------      ------

Held to maturity:
   U.S. Government and agencies        2,790       4,624       5,660
   Obligations of SCM                  3,844       4,782         356
   Mortgage-backed                        43          --       6,161
   Other debt securities                  --          --         204
                                     -------      ------      ------
        Total held to maturity         6,677       9,406      12,381
                                     -------      ------      ------
        Total securities             $22,890      26,676      18,910
                                     =======      ======      ======
</TABLE>

     The following table indicates, for the year ended December 31, 1999, the
amount of investments due in (1) one year or less, (2) one to five years, (3)
five to ten years, and (4) over ten years:

<TABLE>
<CAPTION>

                           1 YR OR                                                      OVER 10
                              LESS            1 TO 5 YRS          5 TO 10 YRS             YRS                TOTAL
                           BALANCE    YIELD     BALANCE    YIELD    BALANCE     YIELD   BALANCE    YIELD    BALANCE
                                                                  (Dollars in Thousands)
<S>                       <C>         <C>     <C>          <C>    <C>           <C>     <C>        <C>      <C>
Available for sale:
 U.S. Government
   and agencies           $  989       5.12%    $7,522      5.74%   $1,558      5.93%   $  309       7.5%  $10,378
Obligations of SCM                                 100      5.02       966      4.35     1,661       4.96    2,727
Mortgage-backed                                    498      5.50        85       9.0     1,130       6.6     1,713
Marketable equity
securities(2)                                                                            1,395       6.4     1,395
Held to maturity:
U.S. Government
and agencies                                     2,560      5.78                                             2,560
Obligations of SCM            75       8.10                            155      5.25                           230
Mortgage-backed                                     44      5.54     3,800      7.65        43       5.3     3,887
                           -----                ------               -----               -----              ------

     Totals                1,064                10,724               6,564               4,538              22,890
                           =====                ======               =====               =====              ======
</TABLE>

(1)  Yields are presented based on adjusted cost basis of securities available
     for sale. Yields based on carrying value would be higher since fair value
     is less than adjusted cost.

(2)  Marketable equity securities are included in the over 10 year category as
     there is no maturity.


                                       20
<PAGE>   10

DEPOSITS AND BORROWINGS

     Deposits are our primary source of funding loans. Depending upon current
market rates, we may from time to time use FHLB borrowings to complement our
funding needs. See "--Liquidity" and "--Interest Rate Sensitivity." We believe
we have the ability to generate deposit growth within our local markets as loan
demand dictates. Our long-term strategy has been to match the competition on
popular deposit products such as money market demand accounts and certificates
of deposit. FHLB advances, while more costly than deposit funding, are typically
the lowest cost borrowed funds available to institutions such as our banks. Our
banks utilize short term borrowing from the FHLB to sustain the available for
sale loans until they are sold. The marketable time table has increased
slightly, therefore, short term borrowing have increased. Of a total $39.6
million in FHLB borrowings at year-end 1999, $27.8 million matures before
December 31, 2000.

     Total deposits grew at a rate of 21.8% during 1999, resulting from the
opening of new branch locations, acquiring a new branch location and more
attractive pricing for deposits. Loan growth was greater than deposit growth in
1999, resulting in an increase in loan to deposit ratio from 90% at year end
1998 to 101% at year end 1999. To offset the loan growth, the banks purchased
federal funds of $2.3 million at year end 1999 and short term FHLB funds.

     We operate retail bank branches in nine different Tennessee counties and
have fifty percent (50%) ownership of a stand-alone federal savings bank in one
Kentucky county through a joint venture. Each local market has it own unique
deposit customer base. Deposit growth has been strong in the new communities
where additional branches have been established. In general, large certificate
of deposit customers tend to be more sensitive to interest rate levels, making
these deposits less reliable sources of funding from liquidity planning purposes
than core deposits. We have normally had to pay a small premium for these types
of deposits above current rates. However, we believe that we have long-term
customers who maintain substantial deposits with our banks based upon personal
relationships with each bank's officers and employees.

     Average amount of and average rate paid for our deposits for year-end 1997,
1998, and 1999 are represented by deposit category on the table on pages 23
through 25 of this section of the documents.

     The following table indicates amounts outstanding of time certificates of
deposit of $100,000 or more and respective maturities for the year ended
December 31, 1999:



<TABLE>
<CAPTION>

                                  TIME
                              CERTIFICATES
                               OF DEPOSIT

                             (In thousands)

<S>                              <C>
3 months or less                 20,714

3-6 months                       24,409

6-12 months                      16,272

over 12 months                   21,694
                                 ------
Total                            83,089
                                 ======
</TABLE>


                                       21
<PAGE>   11


                   CUMBERLAND BANCORP, INC. AND SUBSIDIARIES
          Consolidated Average Balance Sheets, Net Interest Revenue and
                 Changes in Interest Income and Interest Expense

     The following table shows the consolidated average monthly balances of each
     principal category of assets, liabilities and stockholders' equity of the
     company, and an analysis of net interest revenue, and the change in
     interest income and interest expense segregated into amounts attributable
     to changes in volume and changes in rates. The table is presented on a
     taxable equivalent basis.

<TABLE>
<CAPTION>

                                                    (Dollars in Thousands)

                                                 1998                            1997                   1998/1997 Change
                                    ------------------------------   ----------------------------- -------------------------
                                     Average   Interest   Revenue/   Average   Interest   Revenue/ Due To    Due To
                                     Balance     Rate     Expense    Balance     Rate     Expense  Volume    Rate (1)  Total
                                     -------     ----     -------    -------     ----     -------  ------    --------  -----

<S>                                 <C>         <C>       <C>        <C>       <C>        <C>      <C>       <C>      <C>
Net loans (2 and 3)                 $293,665    10.22%    29,999     184,792    10.17%    18,791   11,071     137     11,208
                                    --------    -----     ------     -------    -----     ------   ------    ----     ------

Investment Securities:
   Available for Sale                 26,612     6.04%     1,607      14,631     6.40%       937      767     (97)       670
                                                                                                   ------    ----     ------

         Total investment securities  26,612     6.04%     1,607      14,631     6.40%       937      767     (97)       670
                                    --------    -----     ------     -------    -----     ------   ------    ----     ------

Federal funds sold                    16,344     5.14%       840      10,444     4.88%       510      288      42        330
FHLB and FRB stock                     2,541     7.20%       183       1,451     6.82%        99       74      10         84
Interest-bearing deposits in banks    14,575     4.54%       661       2,896     4.90%       142      573     (54)       519
                                    --------    -----     ------     -------    -----     ------   ------    ----     ------

         Total earning assets        353,737     9.41%    33,290     214,214     9.56%    20,479   12,773      38     12,811
                                                =====     ======                =====     ======   ======    ====     ======

Cash and due from banks                7,262                           4,521
Allowance for loan losses             (3,504)                         (2,603)
Other assets                          15,472                          10,088
                                    --------                         -------

         Total assets               $372,967                         226,220
                                    ========                         =======

Deposits:
   NOW investments                  $ 24,919     2.75%       686      17,975     2.69%       483      187      16        203
   Money market investments           59,580     4.90%     2,919      26,719     4.91%     1,313    1,615      (9)     1,606
   Savings                            13,023     3.34%       435       9,399     3.21%       302      116      17        133
   Time deposits $100,000 and over    58,765     5.74%     3,373      34,665     6.15%     2,132    1,482    (241)     1,241
   Other time deposits               140,266     5.88%     8,249      94,442     5.70%     5,387    2,614     248      2,862
                                    --------    -----     ------     -------    -----     ------   ------    ----     ------

         Total interest-bearing
             deposits                296,553     5.28%    15,662     183,200     5.25%     9,617    6,014      31      6,045

Non interest-bearing demand deposits  23,243       --         --      13,019       --         --       --      --         --
                                    --------    -----     ------     -------    -----     ------   ------    ----     ------

         Total deposits              319,796     4.90%    15,662     196,219     4.90%     9,617    6,014      31      6,045

Fed Funds purchased                      164                   5         533     7.50%        40      (28)     (7)       (35)
Note payable                           6,590     8.00%       527       2,994     8.42%       252      303     (28)       275
FHLB advances                         21,022     5.65%     1,187       9,395     5.53%       520        6     661        667
                                    --------              ------     -------               -----   ------    ----     ------
         Total deposits and borrowed

             funds                   347,572     5.00%    17,381     209,141     4.99%    10,429    6,295     657      6,952
                                                -----                           -----                                 ------

Other liabilities                      4,788                           3,536
Stockholders' equity                  20,607                          13,543
                                    --------                         -------

         Total liabilities and
           stockholders' equity     $372,967                         226,220
                                    ========                         =======

Net interest income                                      $15,909                         $10,050    6,478    (619)     5,859
                                                         =======                         =======   ======    ====     ======

Net yield on earning assets                      4.50%                           4.69%
                                                =====                          ======
</TABLE>


1    Changes in interest income and expense not due solely to balance or rate
     changes are included in the rate category.

2    Interest income includes fees on loans of $1,748 in 1998 and $1,025 in
     1997.

3    Nonaccrual loans are included in average loan balances and the associated
     income (recognized on a cash basis) is included in interest.


                                       22
<PAGE>   12




                   CUMBERLAND BANCORP, INC. AND SUBSIDIARIES
         Consolidated Average Balance Sheets, Net Interest Revenue and
                Changes in Interest Income and Interest Expense

                The following table shows the consolidated average monthly
                balances of each principal category of assets, liabilities and
                stockholders' equity of the Company, and an analysis of net
                interest revenue, and the change in interest income and
                interest expense segregated into amounts attributable to
                changes in volume and changes in rates. The table is presented
                on a taxable equivalent basis.

<TABLE>
<CAPTION>
                                                                             (Dollars in Thousands)
                                                          1999                      1998                      1999/1998 CHANGE
                                               -------------------------- --------------------------  ------------------------
                                               Average  Interest Revenue/ Average Interest  Revenue/  Due to  Due to
                                               Balance     Rate  Expense  Balance   Rate    Expense   Volume  Rate (1)   Total
                                               -------- -------- -------- ------- --------  --------  ------  --------   -----

<S>                                            <C>         <C>    <C>     <C>       <C>      <C>       <C>     <C>       <C>
Net loans (2 and 3)                            $374,716    9.75%  36,528  293,665   10.22%   29,999    8,280   (1,751)   6,529
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

Investment securities:
    Available for sale                           25,886    5.80%   1,502   26,612    6.04%    1,607      (44)     (61)    (105)
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

    Total investment securities                  25,886    5.80%   1,502   26,612    6.04%    1,607      (44)     (61)    (105)
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

Federal funds sold                               15,046    4.72%     710   16,344    5.14%      840      (67)     (63)    (130)
FHLB and FRB stock                                2,921    6.85%     200    2,541    7.20%      183       27      (10)      17
Interest-bearing deposits in bank                 7,824    3.23%     253   14,575    4.54%      661     (306)    (102)    (408)
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

        Total earning assets                    426,393    9.19%  39,193  353,737    9.41%   33,290    7,890   (1,987)   5,903
                                                           ====   ======             ====    ======    =====   ======    =====

Cash and due from banks                           8,903                     7,262
Allowance for loan losses                        (4,196)                   (3,504)
Other assets                                     22,278                    15,472
                                               --------                  --------

                Total assets                    453,378                   372,967
                                               ========                  ========

Deposits:
  NOW investments                                35,889    2.38%     854   24,919    2.75%      686      302     (134)     168
Money market investments                         90,045    4.53%   4,082   59,580    4.90%    2,919    1,493     (330)   1,163

     Savings                                     15,090    3.06%     462   13,023    3.34%      435       69      (42)      27
Time deposits $100,000 and                       65,587    5.20%   3,411   58,765    5.74%    3,373      392     (354)      38
                    over
     Other time deposits                        149,464    5.51%   8,241  140,266    5.88%    8,249      541     (549)      (8)
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

        Total interest-bearing
                    deposits                    356,075    4.79%  17,050  296,553    5.28%   15,662    2,797   (1,409)   1,388

Non interest-bearing demand                      31,866      --       --   23,243      --        --       --       --       --
   deposits
                                               --------    ----   ------  -------   -----    ------    -----   ------    -----

              Total deposits                    387,941    4.39%  17,050  319,796    4.90%   15,662    2,797   (1,409)   1,388

Fed Funds purchased                               2,334    5.06%     118      164    3.05%        5       66       47      113
Note payable                                      7,293    7.93%     578    6,590    8.00%      527       56       (5)      51
FHLB advances                                    24,850    5.56%   1,381   21,022    5.65%    1,187        2      192      194
                                               --------           ------  -------            ------    -----   ------    -----

                    Total deposits and
                    borrowed  funds             422,418    4.53%  19,127  347,572    5.00%   17,381    2,921   (1,175)   1,746
                                                           ----                      ----

Other liabilities                                 3,760                0    4,788
Stockholders' equity                             27,200                0   20,607
                                                 ------                    ------
       Total liabilities and
        stockholders' equity                    453,378       0           372,967
                                                =======                   =======

Net interest income                                              $20,066                   $ 15,909    4,969     (812)   4,157
                                                                 =======                   ========    =====     ====    =====

Net yield on earning assets                                4.71%                     4.50%
                                                           ====                      ====
</TABLE>

1    Changes in interest income and expense not due solely to balance or
     rate changes are included in the rate category.

2    Interest income includes fees on loans of $2,551 in 1999 and $1,748 in
     1998.


3    Nonaccrual loans are included in average loan balances and the
     associated income (recognized on a cash basis) is included in
     interest.



                                       23


<PAGE>   13


EQUITY AND CAPITAL RESOURCES

         We were "well capitalized" for leverage and Tier One capital
calculations; we were "adequately capitalized" for total capital to
risk-weighted assets purposes at December 31, 1999. Our leverage capital ratio
was 6.84% in 1999 and 5.45% in 1998, with stockholders' equity of $35.3 million
at year-end 1999. For a discussion of capital requirements see "Supervision and
Regulation - Capital Requirements." We declared a 10% stock dividend in March
1999. Also in March 1999, we sold 100,000 shares of stock for $1,000,000 to a
group of Franklin, Tennessee investors to support the new Franklin branch
opened there by The Community Bank.

         In September 1999, we completed an Initial Public Offering (IPO) of
700,000 shares of stock at a price of $12.50 per share for $8,500,000. In
connection with the purchase of the two branches from a financial institution,
we issued 47,000 shares valued at $588,000. To purchase the minority interest
shares of Bank of Dyer we issued 7,704 shares of stock valued at approximately
$99,000.

         In March 2000, we have declared a .025 cent cash dividend for
shareholders of record as of March 1, 2000 to be paid April 14, 2000.

         Items that represent common stock equivalents include 425,635 shares
of common stock options outstanding at December 31, 1999. At December 31, 1999,
there were 113,540 additional common shares available for grant under the stock
option plan. We plan to continue granting stock options to selected officers,
directors, and other key employees.

RETURN ON EQUITY AND ASSETS

         Returns on average consolidated assets and average consolidated equity
for the periods indicated are as follows:

<TABLE>
<CAPTION>
                                                                                    Years Ended
                                                                                    December 31,
                                                                          1999          1998          1997

<S>                                                                      <C>           <C>           <C>
Return on average assets                                                  0.77%         0.89%         0.94%
Return on average equity                                                 12.91%        16.22%        15.76%
Average equity to average assets ratio                                    6.00%         5.53%         5.99%
Dividend payout ratio                                                       --            --            --
</TABLE>

LIQUIDITY

         It is a primary concern to depositors, creditors, and regulators that
banks demonstrate the ability to have readily available funds sufficient to
repay fully-maturing liabilities. Our liquidity, represented by cash and cash
due from banks, is a result of our operating, investing and financing
activities. In order to insure funds are available at all times, we devote
resources to projecting on a monthly basis the amount of funds that will be
required and maintain relationships with a diversified customer base so funds
are accessible. Liquidity requirements can also be met through short-term
borrowings or the disposition of short-term assets, which are generally matched
to correspond to the maturity of liabilities.

         Our banks have liquidity policies and, in the opinion of management,
the overall liquidity level is considered adequate. Neither we, nor our banks,
are subject to any specific liquidity requirements imposed by regulatory
authorities. Our banks are subject to general Federal Reserve guidelines, which
do not require a minimum level of liquidity. The ratio for average loans to
average deposits for 1998 was 99% and for 1999

                                      24


<PAGE>   14


was 96.6%. We do not know of any trends or demands that are reasonably likely
to result in liquidity increasing or decreasing

INTEREST RATE SENSITIVITY

         A key element in the financial performance of financial institutions
is the level and type of interest rate risk assumed. The single most
significant measure of interest rate risk is the relationship of the repricing
periods of earning assets and interest-bearing liabilities. The more closely
the repricing periods are correlated, the less interest rate risk we assume. In
general, community bank customer preferences tend to push the average repricing
period for costing liabilities to a shorter time frame than the average
repricing period of earning assets, resulting in a net liability sensitive
position in time frames less than one year. A summary of the repricing schedule
of our interest earning assets and interest-bearing liabilities ("GAP") at
year-end 1999 follows:

<TABLE>
<CAPTION>
                                                                          91-365                            OVER 5
                                                     1-90 DAYS             DAYS           1-5 YEARS          YEARS          TOTAL
<S>                                                  <C>                  <C>             <C>               <C>            <C>
Interest earning assets:
   Loans, net                                        $ 173,047            104,196           146,563          16,510        440,316
Securities available for sale                              798              1,625             8,025           5,765         16,213
Securities held to maturity                                793              2,663             2,781             440          6,677
   Federal funds sold                                   11,250                 --                --              --         11,250
   Interest-earning deposits                             4,896                500                --              --          5,396
----------------------------------------------------------------------------------------------------------------------------------
     Total interest earning assets                   $ 190,784            108,984           157,369          22,715        479,852
==================================================================================================================================
Interest bearing liabilities:
   Interest bearing demand dep                       $ 132,917                 --                --              --        132,917
   Savings deposits                                     13,582                 --                --              --         13,582
   Time deposits                                        55,898            136,278            61,618             199        253,993
   FHLB borrowings                                      10,539             16,852             2,154          10,009         39,554
   Notes payable                                            78                975             4,290           2,112          7,455
   Fed Funds purchased                                   2,275                 --                --              --          2,275
----------------------------------------------------------------------------------------------------------------------------------
   Total interest bearing liabilities                $ 215,289            154,105            68,062          12,320        449,776
==================================================================================================================================
Rate sensitive gap                                   $ (24,505)           (45,121)           89,307          10,395         30,076
----------------------------------------------------------------------------------------------------------------------------------
Rate sensitive cumulative gap                          (24,505)           (69,626)           19,681          30,076         30,076
Cumulative gap as a percentage
  of earnings assets                                     (5.11)%           (14.51)%            4.10%           6.27%
==================================================================================================================================
</TABLE>

As shown in the table, we have a cumulative negative GAP of approximately 5.1%
and 14.5% at the end of 90 days and one year, respectively. Management believes
that this level of negative GAP is appropriate since many of the liabilities
which are immediately repriceable can be effectively repriced more slowly than
the assets which are contractually immediately repriceable in a rising rate
environment. Conversely, those liabilities can often be repriced downward more
rapidly than contractually required assets repricing in a downward rate
environment. The degree to which management can control the rate of change in
deposit liabilities, which are immediately repriceable, is affected to a large
extent by the speed and amount of interest rate movements.


                                      25
<PAGE>   15


ITEM 7A  QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK


         Our primary component of market risk is interest rate volatility.
Fluctuations in interest rates will ultimately impact both the level of income
and expense recorded on a large portion of our assets and liabilities, and the
market value of all interest-earning assets and interest-bearing liabilities,
other than those which possess a short term to maturity. Based upon the nature
of our operations, we do not maintain any foreign currency exchange or
commodity price risk.

         The following table provides information about our financial
instruments that are sensitive to changes in interest rates as of December 31,
1999. These market risk sensitive instruments have been entered into by us for
purposes other than trading. We do not hold market risk sensitive instruments
for trading purposes. Amounts described below do not take into account possible
loan, security, or interest bearing deposit renewals or repricing for such
renewals. The information provided by this table should be read in connection
with our audited consolidated financial statements and Management's Discussion
and Analysis of Financial Condition and Results of Operation.


<TABLE>
<CAPTION>
                                                   EXPECTED MATURITY DATE -
                                                   YEAR ENDING DECEMBER 31,

                                                           2001 to       2003 to           2005                             FAIR
(Dollars in Thousands)                        2000          2002          2004          THEREAFTER           TOTAL          VALUE
<S>                                          <C>           <C>           <C>            <C>                  <C>            <C>
EARNING ASSETS:
Loans, net of unearned
interest:(1)
                  Variable rate             $152,639       $11,168       $ 2,703           $    85          $166,595       $166,595
      Average interest rate (%)                 9.51          8.70          8.20              9.33              9.43
                  Fixed rate                 114,020        57,202        86,465            16,034           273,721        272,768
      Average interest rate (%)                 8.97          9.34          9.06              8.36              9.04
Securities(2)                                  1,064         7,440         3,284            11,102            22,890         22,807
                  Average interest (%)          5.12          5.73          5.96              6.45              5.80
Federal funds sold                            11,250                                                          11,250         11,250
                  Average interest (%)          5.60                                                            5.60
Interest-earning deposits                      5,396                                                           5,396         5,396
in financial institutions                       5.50%                                                           5.50%
Interest-bearing deposits                    339,336        47,555        14,063               199           401,153        400,866
                  Average interest (%)          4.96          5.70          5.93              4.75              5.08
Other borrowings                              30,719         3,618         2,826            12,121            49,284         48,009
                  Average interest (%)          5.91          7.17          7.19              5.84
</TABLE>

------------------
(1) Loan amounts and weighted average interest rates for loans net out any
undisbursed loan proceeds, make no assumptions about loan prepayments, and do
not include the allowance for loan losses.

(2) Securities include our investment in obligations of certain political
subdivisions within the State of Tennessee. Average interest rates have not
been adjusted for any federal, state, or municipal tax liability that we may
incur.


                                      26
<PAGE>   16


                                   SIGNATURES

         In accordance with Section 13 or 15(d) of the Exchange Act, the
registrant has duly caused this report to be signed on its behalf by the
undersigned, thereunto duly authorized.

                                CUMBERLAND BANCORP, INCORPORATED
                                (REGISTRANT)



DATE:    April 12, 2000         BY: /s/ Joel Porter
     --------------------          ---------------------------------
                                   Joel Porter, President
                                   (Principal Executive Officer)






                                       59