Kentucky’s series record 5–1. Scores list Kentucky first.
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| Oct 8, 1927 | Kentucky Wesleyan at Kentucky | W | 13–7 | — |
| Oct 1, 1921 | Kentucky Wesleyan at Kentucky | W | 68–0 | — |
| Oct 15, 1910 | Kentucky at Kentucky Wesleyan | W | 42–0 | Winchester |
| Sept 25, 1909 | Kentucky Wesleyan at Kentucky | W | 18–0 | — |
| Sept 21, 1907 | Kentucky at Kentucky Wesleyan | W | 17–0 | Winchester |
| Oct 11, 1897 | Kentucky at Kentucky Wesleyan | L | 0–4 | Winchester |
Game results come from the Kentucky football season archive. Box scores are linked where a game-specific source was verified.