<Page>

                                                                 EXHIBIT 99.CERT

                                                                  Exh. (a)(2)(i)

I, William M. Dutton, certify that:

1. I have reviewed this report on Form N-CSR of Skyline Funds;

2. Based on my knowledge, this report does not contain any untrue statement of a
material fact or omit to state a material fact necessary to make the statements
made, in light of the circumstances under which such statements were made, not
misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial
information included in this report, fairly present in all material respects the
financial condition, results of operations, changes in net assets, and cash
flows (if the financial statements are required to include a statement of cash
flows) of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for
establishing and maintaining disclosure controls and procedures (as defined
in Rule 30a-3(c) under the Investment Company Act of 1940) and internal
control over financial reporting (as defined in Rule 30a-3(d) under the
Investment Company Act of 1940) for the registrant and have:

        (a) Designed such disclosure controls and procedures, or caused such
        disclosure controls and procedures to be designed under our supervision,
        to ensure that material information relating to the registrant,
        including its consolidated subsidiaries, is made known to us by others
        within those entities, particularly during the period in which this
        report is being prepared;

        (b) Designed such internal control over financial reporting, or
        caused such internal control over financial reporting to be designed
        under our supervision, to provide reasonable assurance regarding the
        reliability of financial reporting and the preparation of financial
        statements for external purposes in accordance with generally accepted
        accounting principles;

        (c) Evaluated the effectiveness of the registrant's disclosure controls
        and procedures and presented in this report our conclusions about the
        effectiveness of the disclosure controls and procedures, as of a date
        within 90 days prior to the filing date of this report based on such
        evaluation; and

        (d) Disclosed in this report any change in the registrant's internal
        control over financial reporting that occurred during the registrant's
        most recent fiscal year that has materially affected, or is reasonably
        likely to materially affect, the registrant's internal control over
        financial reporting; and

5. The registrant's other certifying officer and I have disclosed to the
registrant's auditors and the audit committee of the registrant's board of
directors (or persons performing the equivalent functions):

        (a) All significant deficiencies and material weaknesses in the design
        or operation of internal control over financial reporting which are
        reasonably likely to adversely affect the registrant's ability to
        record, process, summarize, and report financial information; and

<Page>

        (b) Any fraud, whether or not material, that involves management or
        other employees who have a significant role in the registrant's internal
        control over financial reporting.

Date: February 28, 2005


/s/ William M. Dutton
- --------------------------------------
William M. Dutton
President and Trustee
(Principal Executive Officer)

<Page>

                                                                 Exh. (a)(2)(ii)

I, Benjamin J. Kim, certify that:

1. I have reviewed this report on Form N-CSR of Skyline Funds;

2. Based on my knowledge, this report does not contain any untrue statement of a
material fact or omit to state a material fact necessary to make the statements
made, in light of the circumstances under which such statements were made, not
misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial
information included in this report, fairly present in all material respects the
financial condition, results of operations, changes in net assets, and cash
flows (if the financial statements are required to include a statement of cash
flows) of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for
establishing and maintaining disclosure controls and procedures (as defined
in Rule 30a-3(c) under the Investment Company Act of 1940) and internal
control over financial reporting (as defined in Rule 30a-3(d) under the
Investment Company Act of 1940) for the registrant and have:

        (a) Designed such disclosure controls and procedures, or caused such
        disclosure controls and procedures to be designed under our supervision,
        to ensure that material information relating to the registrant,
        including its consolidated subsidiaries, is made known to us by others
        within those entities, particularly during the period in which this
        report is being prepared;

        (b) Designed such internal control over financial reporting, or
        caused such internal control over financial reporting to be designed
        under our supervision, to provide reasonable assurance regarding the
        reliability of financial reporting and the preparation of financial
        statements for external purposes in accordance with generally accepted
        accounting principles;

        (c) Evaluated the effectiveness of the registrant's disclosure controls
        and procedures and presented in this report our conclusions about the
        effectiveness of the disclosure controls and procedures, as of a date
        within 90 days prior to the filing date of this report based on such
        evaluation; and

        (d) Disclosed in this report any change in the registrant's internal
        control over financial reporting that occurred during the registrant's
        most recent fiscal year that has materially affected, or is reasonably
        likely to materially affect, the registrant's internal control over
        financial reporting; and

5. The registrant's other certifying officer and I have disclosed to the
registrant's auditors and the audit committee of the registrant's board of
directors (or persons performing the equivalent functions):

        (a) All significant deficiencies and material weaknesses in the design
        or operation of internal control over financial reporting which are
        reasonably likely to adversely affect the registrant's ability to
        record, process, summarize, and report financial information; and

<Page>

        (b) Any fraud, whether or not material, that involves management or
        other employees who have a significant role in the registrant's internal
        control over financial reporting.

Date: February 28, 2005


/s/ Benjamin J. Kim
- --------------------------------------
Benjamin J. Kim
Vice President and Treasurer
(Principal Financial Officer)