Kentucky’s series record 11–7–2. Scores list Kentucky first.
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| Oct 3, 1942 | Washington & Lee at Kentucky | W | 53–0 | — |
| Oct 4, 1941 | Kentucky at Washington & Lee | W | 7–0 | Lex. Va. |
| Oct 5, 1940 | Washington & Lee at Kentucky | W | 47–12 | — |
| Oct 15, 1938 | Washington & Lee at Kentucky | L | 0–8 | — |
| Oct 16, 1937 | Washington & Lee at Kentucky | W | 41–6 | — |
| Oct 17, 1936 | Kentucky at Washington & Lee | W | 39–7 | Lex. Va. |
| Sept 29, 1934 | Washington & Lee at Kentucky | L | 0–7 | — |
| Oct 21, 1933 | Kentucky at Washington & Lee | L | 0–7 | Roanoke |
| Oct 15, 1932 | Washington & Lee at Kentucky | W | 53–7 | — |
| Oct 10, 1931 | Washington & Lee at Kentucky | W | 45–0 | — |
| Oct 18, 1930 | Washington & Lee at Kentucky | W | 33–14 | — |
| Oct 12, 1929 | Washington & Lee at Kentucky | W | 20–6 | — |
| Oct 13, 1928 | Washington & Lee at Kentucky | W | 6–0 | — |
| Oct 22, 1927 | Washington & Lee at Kentucky | L | 0–25 | — |
| Oct 16, 1926 | Washington & Lee at Kentucky | L | 13–14 | — |
| Oct 17, 1925 | Washington & Lee at Kentucky | L | 0–25 | — |
| Oct 18, 1924 | Washington & Lee at Kentucky | L | 7–10 | — |
| Oct 13, 1923 | Washington & Lee at Kentucky | T | 6–6 | — |
| Nov 22, 1899 | Washington & Lee at Kentucky | W | 6–0 | — |
| Nov 21, 1899 | Washington & Lee at Kentucky | T | 0–0 | — |
Game results come from the Kentucky football season archive. Box scores are linked where a game-specific source was verified.