Challenge Cup
| Home Team | Away Team | Score | Date |
|---|---|---|---|
| Cowdenbeath | Kilmarnock II | 4 - 2 | July 30, 2024 |
| Kilmarnock II | Cowdenbeath | 3 - 0 | August 9, 2022 |
| Date | Venue | Opponent | Score | Result |
|---|---|---|---|---|
| Aug 11, 26 | Away | Edinburgh City | 3 - 1 | Loss |
| Sep 27, 25 | Home | Benburb | 1 - 2 | Loss |
| Nov 30, 24 | Home | Brechin | 1 - 1 | Draw |
| Oct 26, 24 | Away | Spartans | 1 - 2 | Win |
| Sep 28, 24 | Home | Rutherglen Glencairn | 3 - 2 | Win |
| Sep 7, 24 | Home | Morton | 0 - 1 | Loss |
| Date | Venue | Opponent | Score | Result |
|---|---|---|---|---|
| Aug 11, 26 | Away | East Kilbride | 5 - 3 | Loss |
| Nov 11, 25 | Away | Annan Athletic | 6 - 0 | Loss |
| Oct 10, 25 | Away | Clyde | 2 - 1 | Loss |
| Sep 23, 25 | Away | Alloa Athletic | 3 - 0 | Loss |
| Sep 6, 25 | Away | Stenhousemuir | 4 - 0 | Loss |
| Aug 26, 25 | Away | East Fife | 3 - 2 | Loss |
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