Kentucky’s series record 7–3–3. Scores list Kentucky first.
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| Sept 30, 1933 | Sewanee at Kentucky | W | 7–0 | — |
| Oct 1, 1932 | Sewanee at Kentucky | W | 18–0 | — |
| Oct 4, 1930 | Sewanee at Kentucky | W | 37–0 | — |
| Oct 24, 1925 | Sewanee at Kentucky | W | 14–0 | — |
| Oct 25, 1924 | Sewanee at Kentucky | W | 7–0 | — |
| Oct 28, 1922 | Sewanee at Kentucky | W | 7–0 | — |
| Oct 29, 1921 | Kentucky at Sewanee | L | 0–6 | Louisville |
| Oct 23, 1920 | Sewanee at Kentucky | T | 6–6 | — |
| Oct 25, 1919 | Kentucky at Sewanee | W | 6–0 | Sewanee |
| Oct 27, 1917 | Kentucky at Sewanee | L | 0–7 | Chattanooga |
| Oct 21, 1916 | Sewanee at Kentucky | T | 0–0 | — |
| Oct 23, 1915 | Sewanee at Kentucky | T | 7–7 | — |
| Oct 31, 1908 | Sewanee at Kentucky | L | 0–12 | — |
Game results come from the Kentucky football season archive. Box scores are linked where a game-specific source was verified.