Kentucky’s series record 17–18–1. Scores list Kentucky first.
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| Sept 17, 2005 | Kentucky at Indiana | L | 14–38 | Bloomington · Box score |
| Sept 18, 2004 | Indiana at Kentucky | W | 51–32 | Box score |
| Sept 20, 2003 | Kentucky at Indiana | W | 34–17 | Bloomington · Box score |
| Sept 14, 2002 | Indiana at Kentucky | W | 27–17 | — |
| Dec 1, 2001 | Kentucky at Indiana | L | 15–26 | Bloomington · Box score |
| Sept 16, 2000 | Indiana at Kentucky | W | 41–34 | — |
| Sept 18, 1999 | Kentucky at Indiana | W | 44–35 | Bloomington |
| Sept 19, 1998 | Indiana at Kentucky | W | 31–27 | — |
| Sept 20, 1997 | Kentucky at Indiana | W | 49–7 | Bloomington |
| Sept 21, 1996 | Indiana at Kentucky | W | 3–0 | — |
| Sept 16, 1995 | Kentucky at Indiana | W | 17–10 | Bloomington |
| Sept 17, 1994 | Indiana at Kentucky | L | 29–59 | — |
| Sept 18, 1993 | Kentucky at Indiana | L | 8–24 | Bloomington |
| Sept 19, 1992 | Indiana at Kentucky | W | 37–25 | — |
| Sept 21, 1991 | Kentucky at Indiana | L | 10–13 | Bloomington |
| Sept 15, 1990 | Indiana at Kentucky | L | 24–45 | — |
| Sept 9, 1989 | Indiana at Kentucky | W | 17–14 | — |
| Sept 17, 1988 | Kentucky at Indiana | L | 15–36 | Bloomington |
| Sept 19, 1987 | Indiana at Kentucky | W | 34–15 | — |
| Sept 15, 1984 | Kentucky at Indiana | W | 48–14 | Bloomington |
| Sept 17, 1983 | Indiana at Kentucky | W | 24–13 | — |
| Sept 20, 1980 | Indiana at Kentucky | L | 30–36 | — |
| Sept 22, 1979 | Kentucky at Indiana | L | 10–18 | Bloomington |
| Sept 28, 1974 | Indiana at Kentucky | W | 28–22 | — |
| Sept 29, 1973 | Kentucky at Indiana | L | 3–17 | Bloomington |
| Sept 30, 1972 | Indiana at Kentucky | L | 34–35 | — |
| Sept 18, 1971 | Kentucky at Indiana | L | 8–26 | Bloomington |
| Sept 20, 1969 | (#14) Indiana at Kentucky | L | 30–58 | — |
| Sept 23, 1967 | Kentucky at Indiana | L | 10–12 | Bloomington |
| Oct 1, 1927 | Indiana at Kentucky | L | 0–21 | — |
| Oct 9, 1926 | Kentucky at Indiana | L | 6–14 | Bloomington |
| Oct 11, 1919 | Indiana at Kentucky | L | 0–24 | — |
| Oct 5, 1918 | Kentucky at Indiana | W | 24–7 | Bloomington |
| Oct 7, 1905 | Kentucky at Indiana | L | 0–29 | Bloomington |
| Oct 8, 1904 | Kentucky at Indiana | W | 12–0 | Bloomington |
| Nov 30, 1893 | Indiana at Kentucky | T | 24–24 | — |
Game results come from the Kentucky football season archive. Box scores are linked where a game-specific source was verified.