Kentucky’s series record 12–4. Scores list Kentucky first.
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| Oct 20, 1944 | VMI at Kentucky | W | 26–2 | — |
| Sept 30, 1939 | VMI at Kentucky | W | 21–0 | — |
| Oct 3, 1936 | VMI at Kentucky | W | 38–0 | — |
| Nov 11, 1933 | VMI at Kentucky | W | 21–6 | — |
| Sept 24, 1932 | VMI at Kentucky | W | 23–0 | — |
| Nov 14, 1931 | Kentucky at VMI | W | 20–12 | Lex. Va. |
| Nov 15, 1930 | VMI at Kentucky | W | 26–0 | — |
| Nov 16, 1929 | Kentucky at VMI | W | 23–12 | Lex. Va. |
| Nov 17, 1928 | VMI at Kentucky | W | 18–6 | — |
| Nov 12, 1927 | Kentucky at VMI | W | 25–0 | Charleston |
| Nov 13, 1926 | Kentucky at VMI | L | 9–10 | Charleston |
| Nov 14, 1925 | Kentucky at VMI | W | 7–0 | Charleston |
| Nov 15, 1924 | VMI at Kentucky | L | 3–10 | — |
| Nov 12, 1921 | Kentucky at VMI | W | 14–7 | Louisville |
| Nov 2, 1912 | VMI at Kentucky | L | 2–3 | — |
| Nov 26, 1892 | Kentucky at VMI | L | 0–34 | Lexington,Va. |
Game results come from the Kentucky football season archive. Box scores are linked where a game-specific source was verified.