<PAGE>   1
                                    FORM 10-Q


                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


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



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

                For the quarterly period ended SEPTEMBER 30, 1999

                                       OR

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


                         Commission file number: 1-13277


                             CNA SURETY CORPORATION
             (Exact name of Registrant as specified in its Charter)


           DELAWARE                                      36-4144905
(State or other jurisdiction of            (I.R.S. Employer Identification No.)
 incorporation or organization)

    CNA PLAZA, CHICAGO, ILLINOIS                            60685
(Address of principal executive offices)                 (Zip Code)

                                 (312) 822-5000
              (Registrant's telephone number, including area code)

Indicate by check mark whether the registrant (1) has filed all reports required
to be filed by Section 13 or 15(d) of the Securities 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


                      APPLICABLE ONLY TO CORPORATE ISSUERS:

Indicate the number of shares outstanding of each of the issuer's classes of
common stock, as of the latest practicable date:

    43,583,085 shares of Common Stock, $.01 par value as of November 5, 1999.


<PAGE>   2


                     CNA SURETY CORPORATION AND SUBSIDIARIES



<TABLE>
<CAPTION>
                                                              INDEX

                                                                                                                         Page
                                                                                                                         ----
<S>        <C>                                                                                                            <C>
 Part I.   Financial Information (Unaudited):

           Item 1.      Condensed Consolidated Financial Statements:

                        Independent Accountants' Report................................................................     3

                        Condensed Consolidated Balance Sheets at September 30, 1999 and
                        at December 31, 1998...........................................................................     4

                        Condensed Consolidated Statements of Income for the Three- and Nine-Months
                         Ended September 30, 1999 and 1998.............................................................     5

                        Condensed Consolidated Statements of Stockholders' Equity for the Nine
                        Months Ended September 30, 1999 and 1998.......................................................     6

                        Condensed Consolidated Statements of Cash Flows for the Nine Months Ended
                        September 30, 1999 and 1998....................................................................     7

                        Notes to Condensed Consolidated Financial Statements at September 30, 1999 ....................     8

           Item 2.      Management's Discussion and Analysis of Financial Condition and
                        Results of Operations..........................................................................    11

 Part II.  Other Information:

           Item 1.      Legal Proceedings..............................................................................    21

           Item 2.      Changes in the Rights of the Company's Security Holders........................................    21

           Item 3.      Defaults Upon Senior Securities................................................................    21

           Item 4.      Submission of Matters to a Vote of Security Holders............................................    21

           Item 5.      Other Information..............................................................................    21

           Item 6.      Exhibits and Reports on Form 8-K ..............................................................    21

</TABLE>

                                       2
<PAGE>   3






INDEPENDENT ACCOUNTANTS' REPORT




To the Board of Directors and Stockholders of
CNA Surety Corporation
Chicago, Illinois

We have reviewed the accompanying condensed consolidated balance sheet of CNA
Surety Corporation and subsidiaries as of September 30, 1999, and the related
condensed consolidated statements of income for the three-month and nine-month
periods ended September 30, 1999 and 1998 and related condensed consolidated
statements of stockholders' equity and cash flows for the nine-month periods
ended September 30, 1999 and 1998. These financial statements are the
responsibility of the Corporation's management.

We conducted our review in accordance with standards established by the American
Institute of Certified Public Accountants. A review of interim financial
information consists principally of applying analytical procedures to financial
data and of making inquiries of persons responsible for financial and accounting
matters. It is substantially less in scope than an audit conducted in accordance
with generally accepted auditing standards, the objective of which is the
expression of an opinion regarding the financial statements taken as a whole.
Accordingly, we do not express such an opinion.

Based on our review, we are not aware of any material modifications that should
be made to such condensed consolidated financial statements for them to be in
conformity with generally accepted accounting principles.

We have previously audited, in accordance with generally accepted auditing
standards, the consolidated balance sheet of CNA Surety Corporation and
subsidiaries as of December 31, 1998, and the related consolidated statements of
income, stockholders' equity, and cash flows for the year then ended (not
presented herein); and in our report dated February 8, 1999, we expressed an
unqualified opinion on those consolidated financial statements. In our opinion,
the information set forth in the accompanying condensed consolidated balance
sheet as of December 31, 1998 is fairly stated, in all material respects, in
relation to the consolidated balance sheet from which it has been derived.



Deloitte & Touche LLP
Chicago, Illinois
November 8, 1999

                                       3

<PAGE>   4


                    CNA SURETY CORPORATION AND SUBSIDIARIES
                     CONDENSED CONSOLIDATED BALANCE SHEETS
                 (AMOUNTS IN THOUSANDS, EXCEPT PER SHARE DATA)

<TABLE>
<CAPTION>
                                                                                              (Unaudited)
                                                                                             September 30,         December 31,
                                                                                                  1999                 1998
                                                                                           -----------------    -----------------
  <S>                                                                                         <C>                  <C>
  ASSETS Invested assets and cash:
    Fixed income securities, at fair value (amortized cost: $442,411 and $418,866)            $  428,353           $  423,914
    Equity securities, at fair value (cost: $14,986 and $0)........................               14,222                   --
    Short-term investments, at cost (approximates fair value)......................               63,373               57,865
    Other investments, at fair value...............................................                5,294                5,830
    Cash                                                                                           5,832               17,746
                                                                                              ----------           ----------
       Total invested assets and cash..............................................              517,074              505,355
  Deferred policy acquisition costs................................................               84,326               74,488
  Insurance receivables:
    Premiums.......................................................................                9,148                8,950
    Reinsurance, including $45,499 and $47,175 from affiliates.....................               53,952               55,350
  Intangible assets (net of accumulated amortization of $11,805 and $7,347)........              157,504              156,062
  Prepaid reinsurance premiums.....................................................                2,275                2,157
  Other assets.....................................................................               20,092               17,008
                                                                                              ----------           ----------
         Total assets..............................................................           $  844,371           $  819,370
                                                                                              ==========           ==========


  LIABILITIES
  Reserves:
    Unpaid losses and loss adjustment expenses.....................................           $  150,192           $  150,020
    Unearned premiums..............................................................              198,762              183,708
                                                                                              ----------           ----------
       Total reserves..............................................................              348,954              333,728
  Long-term debt...................................................................              101,900              113,000
  Current income taxes payable.....................................................               11,550                6,726
  Deferred income taxes, net.......................................................                5,648               10,649
  Reinsurance payables to affiliates...............................................               10,164                1,424
  Payable for securities purchased.................................................                7,128                8,517
  Other liabilities................................................................               32,112               35,429
                                                                                              ----------           ----------
       Total liabilities...........................................................           $  517,456           $  509,473
                                                                                              ----------           ----------

  Commitments and contingencies (See Note 5)


  STOCKHOLDERS' EQUITY
  Preferred stock, par value $.01 per share, 20,000 shares authorized; none issued
    and outstanding................................................................                   --                   --
  Common stock, par value $.01 per share, 100,000 shares authorized; 44,115 shares
  issued and 44,077 shares outstanding at September 30, 1999 and 44,093 issued
  and outstanding at December 31, 1998.............................................                  441                  441
  Additional paid-in capital.......................................................              253,325              253,215
  Retained earnings................................................................               83,484               52,984
  Accumulated other comprehensive income...........................................               (9,862)               3,257
  Treasury stock, at cost..........................................................                 (473)                   -
                                                                                              ----------            ---------
       Total stockholders' equity..................................................              326,915              309,897
                                                                                              ----------            ---------
       Total liabilities and stockholders' equity..................................           $  844,371           $  819,370
                                                                                              ==========           ==========
</TABLE>

The accompanying notes are an integral part of these condensed financial
statements.

                                       4

<PAGE>   5



                    CNA SURETY CORPORATION AND SUBSIDIARIES
                  CONDENSED CONSOLIDATED STATEMENTS OF INCOME
                 (AMOUNTS IN THOUSANDS, EXCEPT PER SHARE DATA)
                                  (UNAUDITED)
<TABLE>
<CAPTION>

                                                                        Three Months Ended                 Nine Months Ended
                                                                          September 30,                      September 30,
                                                                 ------------------------------     ------------------------------
                                                                       1999            1998               1999            1998
                                                                 --------------- --------------     -------------    -------------
  <S>                                                               <C>             <C>               <C>             <C>
  Revenues:
    Net earned premium..........................................    $   72,009      $   69,781        $  209,567      $  191,804
    Net investment income.......................................         6,387           5,366            18,900          18,232
    Net realized investment gains...............................             6             178               426             222
                                                                    ----------      ----------        ----------      ----------
                                                                        78,402          75,325           228,893         210,258
                                                                    ----------      ----------        ----------      ----------

  Expenses:
    Net losses and loss adjustment expenses.....................         9,447          12,552            33,119          34,328
    Net commissions, brokerage and other underwriting...........        42,661          40,944           124,477         113,712
    Interest expense............................................         1,464           1,847             4,284           5,505
    Amortization of intangible assets...........................         1,508           1,475             4,458           4,425
                                                                    ----------      ----------        ----------      ----------
                                                                        55,080          56,818           166,338         157,970
                                                                    ----------      ----------        ----------      ----------

  Income before income taxes....................................        23,322          18,507            62,555          52,288
  Income taxes..................................................         8,118           7,025            21,470          19,834
                                                                    ----------      ----------        ----------      ----------
  Net income....................................................    $   15,204      $   11,482        $   41,085      $   32,454
                                                                    ==========      ==========        ==========      ==========

  Earnings per share............................................    $     0.34      $     0.26        $     0.93      $     0.74
                                                                    ==========      ==========        ==========      ==========

  Earnings per share, assuming dilution.........................    $     0.34      $     0.26        $     0.93      $     0.74
                                                                    ==========      ==========        ==========      ==========

  Weighted average shares outstanding...........................        44,102          44,033            44,100          43,598
                                                                    ==========      ==========        ==========      ==========

  Weighted average shares outstanding, assuming dilution........        44,261          44,155            44,245          43,764
                                                                    ==========      ==========        ==========      ==========
</TABLE>

The accompanying notes are an integral part of these condensed financial
statements.

                                       5

<PAGE>   6


                    CNA SURETY CORPORATION AND SUBSIDIARIES
           CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS' EQUITY
                             (AMOUNTS IN THOUSANDS)
                                   (UNAUDITED)

<TABLE>
<CAPTION>

                                                                     Common
                                                                     Stock                     Additional
                                                                     Shares        Common       Paid-In      Comprehensive
                                                                  Outstanding      Stock        Capital          Income
                                                                  -------------  -----------   -----------   ---------------
<S>                                                               <C>             <C>            <C>          <C>
Balance, December 31, 1997 ....................................       43,320      $     433      $ 244,829
Comprehensive income:
  Net income ..................................................           --             --             --       32,454
Other comprehensive income:
  Change in unrealized gains on securities (after incometaxes),
  net of reclassification adjustment of $121 ..................           --             --             --        5,977
                                                                                                              ---------
     Total comprehensive income ...............................                                               $  38,431
                                                                                                              =========

Issuance of common stock ......................................          628              6          7,526
Stock options exercised .......................................          138              2            824
                                                                   ---------      ---------      ---------
Balance, September 30, 1998 ...................................       44,086      $     441      $ 253,179
                                                                   =========      =========      =========

Balance, December 31, 1998 ....................................       44,093      $     441      $ 253,215
Comprehensive income:
  Net income ..................................................           --             --             --    $  41,085
Other comprehensive income:
  Change in unrealized gains (losses) on securities (after
income taxes), net of reclassification adjustment of $813 .....           --             --             --      (13,119)
                                                                                                              ---------
     Total comprehensive income ...............................                                               $  27,966
                                                                                                              =========

Issuance of common stock ......................................           --             --             --
Purchase of treasury stock ....................................          (38)            --             --
Stock options exercised .......................................           22             --            110
Dividends paid to stockholders ................................           --             --             --
                                                                   ---------      ---------      ---------
Balance, September 30, 1999 ...................................       44,077      $     441      $ 253,325
                                                                   =========      =========      =========



<CAPTION>

                                                                               Accumulated
                                                                                 Other                          Total
                                                                  Retained   Comprehensive    Treasury      Stockholders'
                                                                  Earnings       Income        Stock           Equity
                                                                 --------------------------- ----------- --------------
<S>                                                               <C>          <C>           <C>            <C>
Balance, December 31, 1997 ....................................   $  10,996    $    474      $       --     $ 256,732
Comprehensive income:
  Net income ..................................................      32,454          --              --        32,454
Other comprehensive income:
  Change in unrealized gains on securities (after incometaxes),
  net of reclassification adjustment of $121 ..................          --       5,977              --         5,977

     Total comprehensive income ...............................

Issuance of common stock ......................................          --          --              --         7,532
Stock options exercised .......................................          --          --              --           826
                                                                  ---------    --------       ---------      --------
Balance, September 30, 1998 ...................................   $  43,450    $  6,451              --     $ 303,521
                                                                  =========    ========       =========     =========

Balance, December 31, 1998 ....................................   $  52,984       3,257      $       --     $ 309,897
Comprehensive income:
  Net income ..................................................      41,085          --              --        41,085
Other comprehensive income:
  Change in unrealized gains (losses) on securities (after
income taxes), net of reclassification adjustment of $813 .....          --     (13,119)             --       (13,119)

     Total comprehensive income ...............................

Issuance of common stock ......................................          --          --              --            --
Purchase of treasury stock ....................................          --          --            (473)         (473)
Stock options exercised .......................................          --          --              --           110
Dividends paid to stockholders ................................     (10,585)         --              --       (10,585)
                                                                  ---------    --------       ---------     ---------
Balance, September 30, 1999 ...................................    $ 83,484    $ (9,862)      $    (473)    $ 326,915
                                                                  =========    ========       =========     =========

</TABLE>

The accompanying notes are an integral part of these condensed financial
statements.


                                       6
<PAGE>   7


                    CNA SURETY CORPORATION AND SUBSIDIARIES
                CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS
                             (AMOUNTS IN THOUSANDS)
                                  (UNAUDITED)
<TABLE>
<CAPTION>
                                                                                                      Nine Months Ended
                                                                                                        September 30,
                                                                                           ------------------------------------
                                                                                                  1999                 1998
                                                                                           -----------------    ---------------
  <S>                                                                                         <C>                  <C>
  OPERATING ACTIVITIES:

    Net income.....................................................................           $   41,085           $   32,454
    Adjustments to reconcile net income to net cash provided by operating activities:
       Depreciation and amortization...............................................                5,939                5,869
       Accretion of bond discount, net.............................................                1,630                1,455
       Net realized investment gains...............................................                 (426)                (222)
    Changes in:
       Insurance receivables.......................................................                1,200              (14,677)
       Reserve for unearned premiums...............................................               15,054               11,225
       Reserve for unpaid losses and loss adjustment expenses......................                  172               16,200
       Deferred policy acquisition costs...........................................               (9,838)              (8,302)
       Deferred income taxes, net..................................................                2,027                4,762
       Reinsurance payables........................................................                8,740                  892
       Other assets and liabilities................................................                  775                 (447)
                                                                                              ----------           ----------

         Net cash provided by operating activities.................................               66,358               49,209
                                                                                              ----------           ----------

  INVESTING ACTIVITIES:
    Fixed income securities:
       Purchases...................................................................             (154,212)            (237,149)
       Maturities..................................................................               31,195               40,464
       Sales.......................................................................               98,267               42,895
    Purchase of equity securities..................................................              (15,145)                  --
    Proceeds from sale of equity securities........................................                  161                   --
    Changes in short-term investments..............................................               (5,508)             100,428
    Acquisition of businesses, net of cash acquired................................               (5,900)                  --
    Other, net.....................................................................               (5,036)              (2,419)
                                                                                              ----------           ----------

         Net cash (used in) investing activities...................................              (56,178)             (55,781)
                                                                                              ----------           ----------

  FINANCING ACTIVITIES:
    Principal payments on long-term debt...........................................              (13,000)                  --
    Proceeds from long-term debt...................................................                1,900                   --
    Issuance of common stock.......................................................                   --                7,532
    Dividends to stockholders......................................................              (10,585)                  --
    Purchase of treasury stock.....................................................                 (473)                  --
    Other..........................................................................                   64                  479
                                                                                              ----------           ----------

         Net cash (used in) provided by financing activities.......................              (22,094)               8,011
                                                                                              ----------           ----------

  (Decrease) Increase in cash......................................................              (11,914)               1,439
  Cash at beginning of period......................................................               17,746                  130
                                                                                              ----------           ----------
  Cash at end of period............................................................           $    5,832           $    1,569
                                                                                              ==========           ==========

  Supplemental Disclosure of Cash Flow Information:
    Cash paid during the period for:
       Interest....................................................................           $    4,853           $    5,415
       Income taxes................................................................           $   13,800           $   12,500
</TABLE>

The accompanying notes are an integral part of these condensed financial
statements.

                                       7

<PAGE>   8


                     CNA SURETY CORPORATION AND SUBSIDIARIES

              NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
                               SEPTEMBER 30, 1999
                                   (UNAUDITED)

1.   SIGNIFICANT ACCOUNTING POLICIES

Principles of Consolidation
     These condensed consolidated financial statements include the accounts of
CNA Surety Corporation and all majority-owned subsidiaries.

Estimates
     The preparation of financial statements in conformity with generally
accepted accounting principles requires management to make estimates and
assumptions that affect the reported amounts of assets and liabilities and
disclosure of contingent assets and liabilities at the date of financial
statements and the reported amounts of revenues and expenses during the
reporting period. Actual results could differ from those estimates.

Basis of Presentation
     These unaudited Condensed Consolidated Financial Statements should be read
in conjunction with the Consolidated Financial Statements and Notes thereto
included in the Company's 1998 Annual Report to Shareholders. Certain financial
information that is normally included in annual financial statements prepared in
accordance with generally accepted accounting principles has been condensed or
omitted as it is not required for interim reporting. The accompanying unaudited
Condensed Consolidated Financial Statements reflect, in the opinion of
management, all adjustments necessary for a fair presentation of the interim
financial statements. All such adjustments are of a normal and recurring nature.
The financial results for interim periods may not be indicative of financial
results for a full year. Certain reclassifications have been made to the 1998
Financial Statements to conform with the presentation in the 1999 Condensed
Consolidated Financial Statements.

Accounting Changes
     In March 1998, the American Institute of Certified Public Accountants'
Accounting Standards Executive Committee ("AcSEC") issued Statement of Position
("SOP") 98-1, "Accounting for the Costs of Computer Software Developed or
Obtained for Internal Use," which provides guidance on accounting for costs of
computer software developed or obtained for internal use and for determining
whether computer software is for internal use. For the purposes of the SOP,
internal-use software is software acquired, internally developed or modified
solely to meet the entity's internal needs for which no substantive plan exists
or is being developed to market the software externally during the software's
development or modification. Accounting treatment for costs associated with
software developed or obtained for internal use, as defined by this SOP, is
based upon a number of factors, including the point in time during the project
that costs are incurred as well as the types of costs incurred. The Company has
adopted this standard effective January 1, 1999; such adoption did not have a
material impact on the Company's financial position and results of operations.

     In April 1998, AcSEC issued SOP 98-5, "Reporting on the Costs of Start-Up
Activities," which provides guidance on the financial reporting of start-up
costs and organization costs. It requires that costs of start-up activities and
organization costs, as defined, be expensed as incurred. The Company has adopted
this standard effective January 1, 1999; such adoption did not have a material
impact on the

                                       8
<PAGE>   9


Company's financial position and results of operations.

     In October 1998, AcSEC issued SOP 98-7, "Deposit Accounting: Accounting for
Insurance and Reinsurance Contracts That Do Not Transfer Insurance Risk," which
provides accounting guidance for insurance and reinsurance contracts that do not
transfer insurance risk, excluding long-duration life and health insurance
contracts. The Company has adopted this standard effective January 1, 1999; such
adoption did not have a material impact on the Company's financial position and
results of operations.

3.   INVESTMENTS

     The amortized cost and estimated fair value of fixed income and equity
securities held by CNA Surety at September 30, 1999 and December 31, 1998, by
investment category, were as follows (dollars in thousands):

<TABLE>
<CAPTION>



                                                                               Gross               Gross
                                                      Amortized Cost or      Unrealized         Unrealized        Estimated Fair
  September 30, 1999                                         Cost              Gains               Losses             Value
  --------------------------------------------------- -------------------------------------- ------------------ -------------------
  <S>                                                  <C>                 <C>                <C>                 <C>
  Fixed income securities:
  U.S. Treasury securities and obligations of U.S.
    Government and agencies:
       U.S. Treasury.............................       $   17,103         $       62          $       (4)        $   17,161
       U.S. Agencies.............................           48,167                  6              (1,001)            47,172
       Collateralized mortgage obligations.......            2,513                 10                  (7)             2,516
       Mortgage pass-through securities..........           47,297                  1              (1,056)            46,242
  Obligations of states and political subdivisions         229,713                 19              (8,965)           220,767
  Corporate bonds................................           43,155                 --              (2,451)            40,704
  Non-agency collateralized mortgage obligations.           13,957                 --                (217)            13,740
  Other asset-backed securities:
    Second mortgages/home equity loans...........           24,255                 69                 (71)            24,253
    Credit card receivables......................            7,999                  8                (176)             7,831
    Other........................................            8,252                 --                (285)             7,967
                                                        ----------         ----------          ----------         ----------
       Total fixed income securities.............          442,411                175             (14,233)           428,353

  Equity securities..............................           14,986                419              (1,183)            14,222
                                                        ----------         ----------          ----------         ----------
       Total.....................................       $  457,397         $      594          $  (15,416)        $  442,575
                                                        ==========         ==========          ==========         ==========

                                                                               Gross               Gross
                                                      Amortized Cost or      Unrealized         Unrealized        Estimated Fair
  December 31, 1998                                          Cost              Gains               Losses             Value
  --------------------------------------------------- -------------------------------------- ------------------ -------------------
  Fixed income securities:
  U.S. Treasury securities and obligations of U.S.
    Government and agencies:
       U.S. Treasury.............................       $   19,009         $      412          $       --         $   19,421
       U.S. Agencies.............................           68,922              2,189                  --             71,111
       Collateralized mortgage obligations.......           17,741                 78                 (76)            17,743
       Mortgage pass-through securities..........           24,834                172                  (1)            25,005
  Obligations of states and political subdivisions         206,264              2,329                (355)           208,238
  Corporate bonds................................           36,538                686                (465)            36,759
  Non-agency collateralized mortgage obligations.           18,811                 32                (149)            18,694
  Other asset-backed securities:
    Second mortgages/home equity loans...........           12,169                219                  (1)            12,387
    Credit card receivables......................            4,896                  5                  (3)             4,898
    Other........................................            9,682                 24                 (48)             9,658
                                                        ----------         ----------          -----------        ----------
       Total fixed income securities.............          418,866              6,146              (1,098)           423,914

  Equity securities..............................               --                 --                  --                 --
                                                        ----------         ----------          ----------         ----------
       Total.....................................       $  418,866         $    6,146          $   (1,098)        $  423,914
                                                        ==========         ==========          ==========         ==========

</TABLE>










                                       9
<PAGE>   10


4.   REINSURANCE

     The effect of reinsurance on the Company's written and earned premium was
as follows (dollars in thousands):

<TABLE>
<CAPTION>


                                                                            Nine Months Ended September 30,
                                                                -------------------------------------------------------
                                                                          1999                          1998
                                                                -------------------------    --------------------------
                                                                   Written       Earned        Written         Earned
                                                                -----------   -----------    -----------   ------------
<S>                                                             <C>           <C>            <C>           <C>
Direct........................................................  $    82,453   $    76,982    $    80,495   $     76,699
Assumed from affiliates.......................................      147,970       137,743        130,381        120,902
Ceded.........................................................       (5,920)       (5,158)        (6,060)        (5,797)
                                                                -----------   -----------    -----------    -----------
                                                                $   224,503   $   209,567    $   204,816    $   191,804
                                                                ===========   ===========    ===========    ===========
</TABLE>


     The effect of reinsurance on the Company's provision for loss and loss
adjustment expenses was as follows (dollars in thousands):


<TABLE>
<CAPTION>
                                                                                                Nine Months Ended
                                                                                                   September 30,
                                                                                           --------------------------
                                                                                              1999            1998
                                                                                           -----------    -----------
<S>                                                                                        <C>            <C>
Gross loss and loss adjustment expense..................................................   $    39,063    $    39,497
Ceded amounts...........................................................................        (5,944)        (5,169)
                                                                                           -----------    -----------
Net loss and loss adjustment expense....................................................   $    33,119    $    34,328
                                                                                           ===========    ===========
</TABLE>

5.   LEGAL PROCEEDINGS

     The Company and its subsidiaries are parties to various lawsuits arising in
the normal course of business, some seeking material damages. The Company
believes the resolution of these lawsuits will not have a material adverse
effect on its financial condition or its results of operations.


                                       10

<PAGE>   11


                     CNA SURETY CORPORATION AND SUBSIDIARIES

           MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION
                            AND RESULTS OF OPERATIONS


GENERAL

     The following is a discussion and analysis of CNA Surety Corporation ("CNA
Surety" or the "Company") and its insurance subsidiaries' operating results,
liquidity and capital resources, and financial condition. This discussion should
be read in conjunction with the Consolidated Financial Statements of CNA Surety
and notes thereto.

FORMATION OF CNA SURETY AND MERGER

     In December 1996, CNA Financial Corporation ("CNAF") and Capsure agreed to
merge (the "Merger") the surety business of CNAF with Capsure's insurance
subsidiaries, Western Surety Company ("Western Surety") and Universal Surety of
America ("USA"), into a newly-formed holding company, CNA Surety Corporation.
CNAF, through its operating subsidiaries, writes multiple lines of property and
casualty insurance, including surety business that is reinsured by Western
Surety. CNAF owns approximately 61% of the outstanding common stock of CNA
Surety. Loews Corporation owns approximately 86% of the outstanding common stock
of CNAF. The principal operating subsidiaries of CNAF that wrote the surety line
of business for their own account prior to the Merger were Continental Casualty
Company and its property and casualty affiliates (collectively, "CCC") and The
Continental Insurance Company and its property and casualty affiliates
(collectively, "CIC"). CIC was acquired by CNAF on May 10, 1995. The combined
surety operations of CCC and CIC are referred to herein as CCC Surety Operations
("Predecessor").

     Pursuant to a reorganization agreement, CCC Surety Operations and Capsure
merged their respective operations at the close of business on September 30,
1997 ("Merger Date"). CNAF, through its property and casualty subsidiaries, CCC
and CIC, contributed $52.25 million of capital to CNA Surety. Through
reinsurance agreements, CCC and CIC ceded to Western Surety all of their net
unearned premiums and loss and loss adjustment expense reserves, as of the
Merger Date, and will cede to Western Surety all surety business written or
renewed by CCC and CIC for a period of five years thereafter. Further, CCC and
CIC have agreed to assume the obligation for any adverse development on recorded
reserves for CCC Surety Operations as of the Merger Date, to limit the loss
ratio on certain defined business written by CNA Surety through December 31,
2000, and to provide certain additional excess of loss reinsurance. CCC also
agreed to provide certain administrative services at specified rates, subject to
inflationary increases, for three years after the Merger, if CNA Surety chooses
to purchase such services.

BUSINESS

     The Company primarily operates in the surety and fidelity segment of the
domestic property and casualty insurance industry. CNA Surety's insurance
subsidiaries write surety and fidelity bonds in all 50 states through a combined
network of approximately 37,000 independent agencies. CNA Surety's principal
insurance subsidiaries are Western Surety and USA. Western Surety writes, on a
direct basis or as business assumed from CCC and CIC, small fidelity and
non-contract surety bonds, referred to as commercial bonds; small, medium and
large contract bonds; international surety and credit insurance; and errors and
omissions ("E&O") liability insurance, as a licensed insurer in all 50 states
and the District of
                                       11
<PAGE>   12

Columbia. Western Surety's affiliated company, Surety Bonding Company of America
("SBCA"), writes principally small commercial surety business and is licensed in
23 states. USA specializes in the underwriting of small contract and commercial
surety bonds. USA is licensed in 43 states and the District of Columbia with
most of its business generated in Texas.

     The Company's corporate objective is to be the leading provider of surety
and surety-related products in the United States and in selected international
markets and to be the surety of choice for its customers and independent agents
and brokers.

"SAFE HARBOR" STATEMENT UNDER THE PRIVATE SECURITIES LITIGATION REFORM ACT
OF 1995

The statements which are not historical facts contained in this Form 10-Q are
forward-looking statements that involve risks and uncertainties, including, but
not limited to, product and policy demand and market response risks, the effect
of economic conditions, the impact of competitive products, policies and
pricing, product and policy development, regulatory changes and conditions,
rating agency policies and practices, development of claims and the effect on
loss reserves, the performance of reinsurance companies under reinsurance
contracts with the Company, investment portfolio developments and reaction to
market conditions, the results of financing efforts, the actual closing of
contemplated transactions and agreements, the effect of the Company's accounting
policies, and other risks detailed in the Company's Securities and Exchange
Commission filings. No assurance can be given that the actual results of
operations and financial condition will conform to the forward-looking
statements contained herein.

RESULTS OF OPERATIONS

CNA SURETY RESULTS FOR THE THREE- AND NINE- MONTH PERIODS
ENDED SEPTEMBER 30, 1999 AND 1998

     The components of net income for the Company for the three and nine months
ended September 30, 1999 and 1998 are summarized as follows (dollars in
thousands, except per share amounts):

<TABLE>
<CAPTION>

                                                                   Three Months Ended              Nine Months Ended
                                                                      September 30,                  September 30,
                                                             ------------------------------ -------------------------------
                                                                   1999           1998            1999            1998
                                                             ------------------------------ --------------- ---------------
      <S>                                                       <C>            <C>             <C>             <C>
      Total revenues................................            $   78,402     $   75,325      $  228,893      $  210,258
                                                                ==========     ==========      ==========      ==========

      Underwriting income...........................            $   19,901     $   16,285      $   51,971      $   43,764
      Net investment income.........................                 6,387          5,366          18,900          18,232
      Net investment gains..........................                     6            178             426             222
      Interest expense..............................                 1,464          1,847           4,284           5,505
      Amortization of intangible assets.............                 1,508          1,475           4,458           4,425
                                                                ----------     ----------      ----------      ----------
      Income before income taxes....................                23,322         18,507          62,555          52,288
      Income taxes..................................                 8,118          7,025          21,470          19,834
                                                                ----------     ----------      ----------      ----------
      Net income....................................            $   15,204     $   11,482      $   41,085      $   32,454
                                                                ==========     ==========      ==========      ==========

      Net income per share..........................            $     0.34     $     0.26      $     0.93      $     0.74
                                                                ==========     ==========      ==========      ==========
</TABLE>


                                       12
<PAGE>   13


     Insurance Underwriting

     Underwriting results for the Company for the three and nine months ended
September 30, 1999 and 1998 are summarized in the following table (dollars in
thousands):

<TABLE>
<CAPTION>

                                                                  Three Months Ended              Nine Months Ended
                                                                      September 30,                  September 30,
                                                             ------------------------------ -------------------------------
                                                                   1999           1998            1999            1998
                                                             -------------- --------------- --------------- ---------------
      <S>                                                       <C>            <C>             <C>             <C>
      Gross written premiums........................            $  80,718      $  71,883       $ 230,423       $ 210,876
                                                                =========      =========       =========       =========

      Net written premium...........................            $  78,968      $  69,871       $ 224,503       $ 204,816
                                                                =========      =========       =========       =========

      Net earned premium............................            $  72,009      $  69,781       $ 209,567       $ 191,804
      Net losses and loss adjustment expenses.......                9,447         12,552          33,119          34,328
      Net commissions, brokerage and other..........               42,661         40,944         124,477         113,712
                                                                ---------      ---------       ---------       ---------
      Underwriting income...........................            $  19,901      $  16,285       $  51,971       $  43,764
                                                                =========      =========       =========       =========

      Loss ratio....................................                 13.1%          18.0%           15.8%           17.9%
      Expense ratio.................................                 59.3           58.7            59.4            59.3
                                                                ---------      ---------       ---------       ---------
      Combined ratio................................                 72.4%          76.7%           75.2%           77.2%
                                                                =========      =========       =========       =========
</TABLE>

     Premiums Written

     CNA Surety primarily markets contract and commercial surety bonds. Contract
bonds guarantee obligations covered by a written agreement between two parties.
The most common types include bid, performance and payment bonds. The commercial
surety market includes numerous types of bonds categorized as court judicial,
court fiduciary, public official, license and permit and many miscellaneous
bonds that include guarantees of financial performance. The Company also writes
fidelity bonds which cover losses arising from employee dishonesty and errors
and omissions ("E&O") liability insurance.

     Gross written premiums are shown in the table below (dollars in thousands):

<TABLE>
<CAPTION>

                                                                   Three Months Ended              Nine Months Ended
                                                                      September 30,                  September 30,
                                                             ------------------------------ -------------------------------
                                                                   1999           1998            1999            1998
                                                             ------------------------------ --------------- ---------------
      <S>                                                       <C>            <C>             <C>             <C>
      Contract......................................            $   43,835     $   36,718      $  113,552      $   99,804
      Commercial....................................                30,680         29,316          96,947          91,993
      Fidelity......................................                 4,601          4,349          14,009          13,347
      E&O and other.................................                 1,602          1,500           5,915           5,732
                                                                ----------     ----------      ----------      ----------
                                                                $   80,718     $   71,883      $  230,423      $  210,876
                                                                ==========     ==========      ==========      ==========
</TABLE>

     Gross written premiums increased 12.3%, or $8.8 million, for the three
months ended September 30, 1999 over the comparable period in 1998. Contract
surety accounted for most of this increase with growth of 19.4%, or $7.1
million, in gross written premiums as compared to 1998. This increase reflects
increased volume from new accounts added during the prior eighteen months,
increased direct international premium of $4.4 million and generally healthy
economic conditions for public construction nationwide. The highway/bridge
sector has shown particular strength since the United States Congressional
passage of The Transportation Equity Act for the 21st Century (TEA-21). TEA-21
authorizes a 40% increase in total Federal funding for highway and transit
systems to over $200 billion in the nine year period from 1998 to 2004.
Commercial surety increased 4.7%, or $1.4 million, for the three months ended
September 30, 1999 primarily reflecting increased premiums from the Company's
international surety and credit reinsurance business. CNA Surety assumed $3.0
million and $2.5 million of international surety and credit business for

                                       13

<PAGE>   14


the three months ended September 30, 1999 and 1998, respectively, through a
quota share reinsurance treaty with an affiliate of CCC, CNA Reinsurance Company
Limited (London) ("CNA Re"). Commercial surety, exclusive of international
surety and credit business, increased 3.2% for the three months ended September
30, 1999 as compared to the same period in 1998. The fidelity, E&O and other
book of business increased 6.1%, or $0.4 million, to $6.2 million for the three
months ended September 30, 1999 as compared to the same period in 1998.

     Gross written premiums for the first nine months of 1999 increased 9.3%, or
$19.5 million, compared to the same period in 1998. Contract surety and
commercial surety gross written premiums increased 13.8% and 5.4%, respectively,
for the first nine months of 1999. CNA Surety assumed $8.3 million and $7.5
million of international surety and credit business for the nine months ended
September 30, 1999 and 1998, respectively, through a quota share reinsurance
treaty with CNA Re. The fidelity E&O and other book of business increased 4.4%,
or $0.8 million, for the nine months ended September 30, 1999 as compared to the
same period in 1998.

     Net written premiums are shown in the table below (dollars in thousands):
<TABLE>
<CAPTION>


                                                                   Three Months Ended              Nine Months Ended
                                                                      September 30,                  September 30,
                                                             ------------------------------ -------------------------------
                                                                   1999           1998            1999            1998
                                                             ------------------------------ --------------- ---------------
       <S>                                                       <C>            <C>             <C>             <C>
      Contract......................................            $   42,469     $   35,218      $  109,966      $   95,550
      Commercial....................................                30,722         29,262          96,117          91,723
      Fidelity......................................                 4,601          4,339          14,009          13,307
      E&O and other.................................                 1,176          1,052           4,411           4,236
                                                                ----------     ----------      ----------      ----------
                                                                $   78,968     $   69,871      $  224,503      $  204,816
                                                                ==========     ==========      ==========      ==========
</TABLE>

     For the three months ended September 30, 1999, net written premiums
increased 13.0%, or $9.1 million, over the comparable period in 1998, consistent
with the changes in gross written premiums described above. Net written premiums
increased 20.6%, or $7.3 million, for the contract surety business. Commercial
surety net written premiums increased 5.0%, or $1.5 million, for the three
months ended September 30, 1999 compared to the same period in 1998, with
domestic commercial surety up 3.6%. The fidelity, E&O and other book of business
increased 7.2%, or $0.4 million, for the three months ended September 30, 1999
as compared to the same period in 1998.

     For the first nine months of 1999, net written premiums increased 9.6%, or
$19.7 million, over the comparable period in 1998 with contract surety and
commercial surety up 15.1% and 4.8%, respectively. The fidelity, E&O and other
book of business increased 5.0%, or $0.9 million, for the nine months ended
September 30, 1999 as compared to the same period in 1998.


     Underwriting Income

     Underwriting income increased 22.2% to $19.9 million for the three months
ended September 30, 1999 compared to the same period in 1998 primarily
reflecting favorable loss experience. Underwriting income increased 18.8% to
$52.0 million for the nine months ended September 30, 1999 compared to the same
period in 1998. The nine month period to period change in underwriting income
primarily reflects the 9.3% increase in earned premiums along with the favorable
loss experience discussed below.

                                       14

<PAGE>   15


     Loss Ratio

     The loss ratios for the three months ended September 30, 1999 and 1998 were
13.1% and 18.0%, respectively. The loss ratios included $4.7 million and $0.3
million of favorable reserve development for the three months ended September
30, 1999 and 1998, respectively. Excluding the impact of the favorable reserve
development, the loss ratios would have been 19.7% and 18.4% for the three month
periods ended September 30, 1999 and September 30, 1998, respectively. For the
nine months ended September 30, 1999 and 1998, the loss ratios were 15.8% and
17.9%, respectively. The loss ratios included $8.8 million and $1.9 million of
favorable reserve development for the nine months ended September 30, 1999 and
1998, respectively. Excluding the impact of the favorable reserve development,
the loss ratios would have been 20.0% and 18.9% for the nine months periods
ended September 30, 1999 and September 30, 1998, respectively. The increase in
the adjusted loss ratios for the three- and nine-month periods ended September
30, 1999 reflects the change in business mix due to a higher proportion of
standard contract surety. The increased favorable reserve development for the
three- and nine-month periods in 1999 primarily relates to reserve development
for accident years prior to 1997 and reflects higher salvage and subrogation
recoveries received. This recent trend of increased salvage and subrogation
recoveries will be monitored as part of our regular review of loss reserve
levels.

     Expense Ratio

     The expense ratio increased to 59.3% for the three months ended September
30, 1999 compared to 58.7% for the same period in 1998. This increase in the
expense ratio reflects lower net earned premium growth of 3.2% for the third
quarter of 1999 compared to 11.2% in 1998. Operating expenses increased at a
higher rate of 4.2% for the third quarter of 1999. For the nine months ended
September 30, 1999, the expense ratio increased slightly to 59.4% from 59.3% for
the same period in 1998, as net earned premiums increased 9.3% and operating
expenses increased at a slightly higher rate of 9.5%.


     Investment Income

     For the three months ended September 30, 1999, net investment income was
$6.4 million compared to net investment income for the three months ended
September 30, 1998 of $5.4 million. The average pretax yields were 5.1% and 4.7%
for the three months ended September 30, 1999 and 1998, respectively. The
increase in investment income for the three months ended September 30, 1999 is
attributable to higher average invested assets and general interest rate
increases offset by the effects of a higher proportion of the portfolio being
invested in tax exempt securities. Net investment income for the nine months
ended September 30, 1999 and 1998 was $18.9 million and $18.2 million,
respectively. The average pretax yields were 5.1% and 5.5% for the nine months
ended September 30, 1999 and 1998, respectively. The increase in investment
income for the nine months ended September 30, 1999 is a result of a higher
level of invested assets in 1999.

     Net realized investment gains were $6 thousand for the three months ended
September 30, 1999 compared to $178 thousand net realized investment gains for
the same period in 1998. For the nine months ended September 30, 1999, net
realized investment gains were $0.4 million compared to $0.2 million net
realized investment gains for the same period in 1998.

     Analysis of Other Operations

     Amortization expense was $1.5 million for the three months ended September
30, 1999 and 1998. For

                                       15
<PAGE>   16


nine months ended September 30, 1999 and 1998, amortization of intangibles was
$4.5 and $4.4 million, respectively. Intangible assets represent goodwill and
identified intangibles arising from the acquisition of Capsure, goodwill arising
from the May 1995 acquisition of CIC by CNAF that was allocated to the surety
business of CIC and goodwill arising from a subsequent acquisition. Intangible
assets are generally amortized over 30 years.

     On July 28, 1999 CNA Surety acquired certain assets of Clark Bonding
Company, Inc., a Charlotte, North Carolina, insurance agency and brokerage doing
business as The Bond Exchange. The Bond Exchange specializes in the distribution
of surety and fidelity bonds with 1998 premium production of approximately $4
million. Goodwill arising from this acquisition was $5.9 million and will be
amortized over 30 years.

     Interest expense decreased 20.7% for the third quarter of 1999 as compared
to the third quarter in 1998, primarily due to lower debt levels. Average debt
outstanding was $101.3 million for the third quarter in 1999 compared to $118.0
million in the third quarter of 1998. The weighted average interest rate for the
three months ended September 30, 1999 was 5.4% compared to 5.9% for the same
period in 1998. Interest expense decreased 22.2% for the first nine months of
1999 as compared to the same period in 1998, primarily due to lower debt levels.
Average debt outstanding was $104.3 million for the first nine months in 1999
compared to $118.0 million in the first nine months of 1998. The weighted
average interest rate for the nine months ended September 30, 1999 was 5.3%
compared to 5.9% for the same period in 1998.

     Income Taxes

     Income tax expense was $8.1 million and $7.0 million and the effective
income tax rates were 34.8% and 38.0% for the three months ended September 30,
1999 and 1998, respectively. For the nine months ended September 30, 1999 and
1998, income tax expense was $21.5 million and $19.8 million and the effective
income tax rates were 34.3% and 37.9%, respectively. The decline in the
effective income tax rate primarily relates to the aforementioned relative
increase in investments in tax exempt securities.

LIQUIDITY AND CAPITAL RESOURCES

     It is anticipated that the liquidity requirements of CNA Surety will be met
primarily by funds generated from operations. The principal operating cash flow
sources are premiums, investment income, and sales and maturities of
investments. CNA Surety also may generate funds from additional borrowings under
the credit facility described below. The primary cash flow uses are payments for
claims, operating expenses, federal income taxes, debt service on the credit
facility and dividends to CNA Surety stockholders. In general, surety operations
generate premium collections from customers in advance of cash outlays for
claims. Premiums are invested until such time as funds are required to pay
claims and claims adjusting expenses.

     The Company believes that total invested assets, including cash and
short-term investments, are sufficient in the aggregate and have suitably
scheduled maturities to satisfy all policy claims and other operating
liabilities, including income tax sharing payments of its insurance
subsidiaries. At September 30, 1999, the carrying value of the Company's
insurance subsidiaries' invested assets was comprised of $428.4 million of fixed
income securities, $14.2 million of equity securities, $50.0 million of
short-term investments, $5.3 million of other investments and $3.4 million of
cash. At December 31, 1998, the carrying value of the Company's insurance
subsidiaries' invested assets was comprised of $423.9 million of fixed income
securities, $43.4 million of short-term investments, $5.8 million of other
investments and $1.8 million of cash.

                                       16

<PAGE>   17

     Cash flow at the parent company level is derived principally from dividend
and tax sharing payments from its insurance subsidiaries. The principal
obligations at the parent company level are to service debt, pay operating
expenses and pay dividends to stockholders. At September 30, 1999, the parent
company's invested assets consisted of $13.4 million of short-term investments
and $2.4 million of cash. At December 31, 1998, the parent company's invested
assets consisted of $14.5 million of short-term investments and $15.9 million of
cash.

     The Company's consolidated net cash flow provided by operating activities
was $66.4 million for the nine months ended September 30, 1999 and $49.2 million
for the comparable period in 1998.

     On July 28, 1999 CNA Surety acquired certain assets of Clark Bonding
Company, Inc., a Charlotte, North Carolina, insurance agency and brokerage doing
business as The Bond Exchange for $5.9 million. As part of this acquisition, the
Company incurred an additional $1.9 million of debt in the form of a promissory
note. The promissory note matures on July 27, 2004 and has an interest rate of
5.0%.

     CNA Surety's bank borrowings are under a five-year unsecured revolving
credit facility (the "Credit Facility") that provides for borrowings of up to
$130 million. CNA Surety borrowed $105 million as of September 30, 1997 and used
the proceeds to retire the existing Capsure debt of approximately $54 million
and to make a $50 million capital contribution to Western Surety. On October 6,
1997, CNA Surety borrowed an additional $13 million to pay the $10.6 million
closing dividend to Capsure stockholders and other merger-related costs. As of
September 30, 1999, CNA Surety has repaid $18 million of this debt.

     The interest rate on borrowings under the Credit Facility may be fixed, at
CNA Surety's option, for a period of one, two, three, or nine months and is
based on, among other rates, the London Interbank Offered Rate ("LIBOR"), plus
the applicable margin. The margin, including the facility fee, varies based on
CNA Surety's leverage ratio (debt to total capitalization) and ranges from 0.25%
to 0.40%. As of September 30, 1999, the weighted average interest rate was 5.6%
on the $100.0 million of outstanding borrowings. As of December 31, 1998, the
weighted average interest rate was 5.5% on the $113.0 million of outstanding
borrowings.

     The Credit Facility contains, among other conditions, limitations on CNA
Surety with respect to the incurrence of additional indebtedness and requires
the maintenance of certain financial ratios. As of September 30, 1999, the
Company was in compliance with all restrictions and covenants contained in the
Credit Facility agreement. The Credit Facility provides for the payment of all
outstanding principal balances after five years with no required principal
payments prior to such time. Principal prepayments, if any, and interest
payments are expected to be funded primarily through dividends from CNA Surety's
insurance subsidiaries.

     As an insurance holding company, CNA Surety is dependent upon dividends and
other permitted payments from its insurance subsidiaries to pay cash dividends,
if any, as well as to pay operating expenses and meet debt service requirements.
The payment of dividends by the insurance subsidiaries are subject to varying
degrees of supervision by the insurance regulatory authorities in South Dakota
and Texas. In South Dakota, where Western Surety and SBCA are domiciled,
insurance companies may only pay dividends from earned surplus excluding surplus
arising from unrealized capital gains or revaluation of assets. In Texas, where
USA is domiciled, an insurance company may only declare or pay dividends to
stockholders from the insurer's earned surplus. The insurance subsidiaries may
pay dividends without obtaining prior regulatory approval only if such dividend
or distribution (together with dividends or distributions made within the
preceding 12-month period) is less than, as of the end of the immediately
preceding year, the greater of (i) 10% of the insurer's surplus to policyholders
or (ii) statutory net income. In South Dakota, net income includes net realized
capital gains in an amount not to exceed 20% of net unrealized capital gains.
All

                                       17
<PAGE>   18


dividends must be reported to the appropriate insurance department prior to
payment.

     The dividends that may be paid without prior regulatory approval are
determined by formulas established by the applicable insurance regulations, as
described above. The formulas that determine dividend capacity in the current
year are dependent on, among other items, the prior year's ending statutory
surplus and statutory net income. Dividend capacity for 1999 is based on
statutory surplus and income at and for the year ended December 31, 1998.
Without prior regulatory approval in 1999, CNA Surety's insurance subsidiaries
may pay stockholder dividends of $32.7 million in the aggregate. CNA Surety
received $20.0 million in dividends from its insurance subsidiaries during the
first nine months of 1999 and $4.4 million in the first nine months of 1998.

     In accordance with the provisions of intercompany tax sharing agreements
between CNA Surety and its subsidiaries, the tax of each subsidiary shall be
determined based upon each subsidiary's separate return liability, as calculated
in accordance with the Internal Revenue Code of 1986 (the "Code") as amended.
Intercompany tax payments are made at such times as estimated tax payments would
be required by the Internal Revenue Service ("IRS"). CNA Surety received tax
sharing payments from its subsidiaries of $20.7 million for the nine months
ended September 30, 1999 and $19.8 million for the same period in 1998.

     CNA Surety management believes that it will have sufficient available
resources to meet its present capital needs.

IMPACT OF YEAR 2000 ON THE COMPANY

     The widespread use of computer programs, both in the United States and
internationally, that rely on two digit date fields to perform computations and
decision making functions may cause computer systems to malfunction when
processing information involving dates beginning after 1999. Such malfunctions
could lead to business delays and disruptions.

     For several years prior to the Merger, CNAF and Western Surety had each, as
a matter of normal maintenance and system development practices, begun to
address Year 2000 considerations. The Company has continued to participate in
CNAF's Year 2000 activities following the Merger. The Company's internal target
for achieving Year 2000 internal substantial readiness generally coincided with
CNAF's December 1, 1998 target substantial readiness date. Based upon internal
certification achieved as part of the CNAF Year 2000 activities, the Company's
management believes that the Company has accomplished the December 1, 1998
target date for its internal systems identified prior to that date for
anticipated renovation.

     Independent Assessment of Year 2000 Readiness

     In December 1997, the Company engaged an independent information consulting
firm of national standing to perform a limited review and assessment of the
Company's Year 2000 plans. This engagement included collecting and reviewing
existing enterprise-wide and business unit Year 2000 plans and supporting
documentation, reviewing the process for managing critical external agents and
business partners, and determining if timing and coordination efforts appear
reasonable with respect to program testing and enterprise certification. Based
upon the Company's internal examination and the foregoing review and assessment,
the Company has implemented various resulting recommendations, including the
designation of a Year 2000 project manager with broad authority for the
management and coordination of all Year 2000 efforts and the establishment of
regular Year 2000 status reporting by the project manager to senior management
and the board of directors of CNA Surety.



                                       18

<PAGE>   19
     Non-IT Systems Remediation Status

     The Company considers its non-information technology ("non-IT") systems to
consist of essentially two elements: office facilities and communication
systems, including telephone and facsimile systems.

     The Company leases space for home office and branch locations from various
parties, including the Company's Chicago home office and various branch
locations from CNAF pursuant to the Administrative Services Agreement ("ASA").
The Company has confirmed with CNAF and building management for each building
location that reasonable efforts are being undertaken to ensure timely Year 2000
readiness for such facilities and continues to monitor the progress of third
party landlords.

     Communication systems, i.e., telephone switching equipment and facsimile
server systems, are essential to the business operations of CNA Surety. CNAF has
informed the Company that all communications systems provided by CNAF pursuant
to the ASA are anticipated to be Year 2000 ready, and management believes that
USA and Western Surety's separate communication systems will also be Year 2000
ready on a timely basis.

     IT Systems Remediation Status

     The Company has confirmed that information technology ("IT") systems
provided by CNAF pursuant to the ASA have been certified by CNAF as Year 2000
ready.

     With respect to its internal systems, the Company has created plans to
monitor the Year 2000 renovation or replacement of the Company's IT systems.
Several of these systems are deemed to be obsolete and will not be used in a
Year 2000 ready business environment. As a result of a post-Merger Company
initiative to consolidate and centralize disparate technology systems at Western
Surety, Company management decided to combine any needed Year 2000 renovation
effort with Western Surety's modification efforts.

     Year 2000 Readiness

     All existing IT systems undergoing renovation prior to December 1, 1998,
have been internally certified as Year 2000 ready during the fourth quarter of
1998. Nevertheless, due to delays in the development and testing of a new
enterprise wide claims system it had originally intened for implementation
prior to January 1, 2000, the Company has decided to renovate a remaining
non-compliant component of its existing claim system. The renovation of the one
existing claim system component will involve design and testing to confirm its
Year 2000 readiness on a timely basis. However, if such renovation cannot be
completed on a timely basis, the Company does not anticipate any material
adverse impact on the Company's results of operations, financial condition or
liquidity. Likewise, should the Company decide to develop and implement any new
IT systems before January 1, 2000, any such systems will also involve design
and testing to confirm Year 2000 readiness on a timely basis.

     Year 2000 and IT Expenditures

     The Company's enterprise-wide Year 2000 readiness efforts are currently
estimated to cost approximately $655,000 in excess of the cost of ordinary
software upgrades and replacements and will be funded through working capital.
As of September 30, 1999, approximately $464,000 had been incurred in Year
2000-related expenditures. The estimated amount includes expenses incurred or
anticipated to be




                                       19
<PAGE>   20
incurred for third party remediation and testing and additional equipment
hardware purchases to facilitate further testing. The Year 2000 estimated
readiness costs comprised approximately five percent of the Company's total 1998
IT budget, and the remaining Year 2000 estimated readiness costs anticipated to
be expended in 1999 comprise approximately $110,000, or approximately one
percent of the Company's total 1999 IT budget.

     Business Partner Identification and Communication

The Company believes that it has identified and established communication
regarding Year 2000 issues with substantially all of the business partners
management considers to be significant to its operations. Management has not yet
identified any one business partner whose expected failure to achieve timely
Year 2000 readiness will materially and adversely impact the Company's ability
to continue its business operations. However, due to the interdependent nature
of computer systems, the Company may be adversely impacted depending upon
whether it or other entities not affiliated with the Company (vendors and other
business partners) address Year 2000 issues successfully.

     Year 2000-related Risks

     Management believes that the most reasonably likely worst case Year 2000
scenarios involve either failure of all or part of either or both the nation's
telephonic and/or electrical power distribution systems. Due to the general
uncertainty inherent in the Year 2000 problem, resulting in part from the Year
2000 compliance of third parties, the Company is unable to determine with any
degree of certainty the specific potential consequences of the Year 2000
problem. The failure of a third party to correct a material Year 2000 problem,
which affects the Company's business operations, however, could have a material
adverse effect on the Company's results of operations, financial condition and
liquidity.

     Contingency Plan

     The Company has been and continues to be in the process of revising its
overall enterprise contingency plan to address the continuation of key business
processes. This planning considers disruptions in addition to Year 2000-related
failures, such as fire, vandalism, and other perils.

     Company management has concluded that it is not reasonably possible to
continue the Company's business operations without the use of automation and
information technology, such as computers and telephones. Management, for
contingency planning, is developing, as a back up for its main frame computer
capability, existing computer applications that can be operated at stand-alone
computer stations. Management believes that such particular application(s) may
provide a short-term solution that will enable the Company to process, record,
and invoice for transactions, and to store such transactional data until main
frame processing capability is restored. Through Western Surety, the Company
also subscribes to a third party disaster recovery site, although access is
subject to certain conditions and potential allocation among other subscribers.
The Company is taking steps to assure itself of a greater likelihood of
efficient access to the site in the event of a Year 2000-related disruption of
its main frame computer capability. The Company is also having installed a back
up emergency power generator for its Sioux Falls facility that it believes will
become operational prior to January 1, 2000.

     Company Products and Services' Year 2000 Exposures

     Although the Company has not received any claims based on alleged losses
resulting from the Year 2000 issues, there can be no assurance that bond
obligees or insureds will not suffer losses of this type and seek compensation
under the Company's bonds or policies. If any claims are made, the Company's
obligations, if any, will depend upon the facts and circumstances of the claims
and provisions of the bond or policy. At this time, the Company is unable to
determine whether the adverse impact, if any, in connection with the foregoing
circumstances would be material to the Company's results of operations,
financial condition and liquidity.

                                       20

<PAGE>   21


                     CNA SURETY CORPORATION AND SUBSIDIARIES


                           PART II - OTHER INFORMATION

ITEM 1. Legal Proceedings - None.

ITEM 2. Changes in the Rights of the Company's Security Holders - None.

ITEM 3. Defaults Upon Senior Securities - None.

ITEM 4. Submission of Matters to a Vote of Security Holders - None.

ITEM 5. Other Information - None.

ITEM 6. Exhibits and Reports on Form 8-K:
        (a) Exhibits:
            27. Financial Data Schedule.

        (b) Reports on Form 8-K:
            August 4, 1999; CNA Surety Corporation Press Release issued on July
            28, 1999.
            August 4, 1999; CNA Surety Corporation Press Release issued on
            August 2, 1999.
            August 23, 1999; CNA Surety Corporation Press Release issued on
            August 17, 1999.


                                       21
<PAGE>   22


                                   SIGNATURES



     Pursuant to the requirements of the Securities and Exchange Act of 1934,
the Registrant has duly caused this Report to be signed on its behalf by the
undersigned thereunto duly authorized.





                                    CNA SURETY CORPORATION
                                    (Registrant)





                                     /s/ John S. Heneghan
                                     ------------------------------------------
                                     John S. Heneghan
                                     Vice President and Chief Financial Officer









Date:  November 12, 1999