 |  | Kentucky vs. Maryland | |  |
| Date | Game | Result | Score | Notes |
|---|---|---|---|---|
| 3/22/2002 | (#16) Kentucky vs. (#4) Maryland | L | 68 - 78 | NCAA Tournament East Regional (at Syracuse, NY) |
| 12/11/1999 | (#23) Kentucky at (#21) Maryland | L | 66 - 72 | - |
| 11/24/1999 | (#11) Kentucky vs. (#22) Maryland | W | 61 - 58 | Preseason NIT (at New York, NY) |
| 12/12/1998 | (#2) Maryland at (#5) Kentucky | W | 103 - 91 | - |
| 11/24/1995 | (#1) Kentucky vs. (#14) Maryland | W | 96 - 84 | Tip-off Classic (at Springfield, MA) |
| 3/20/1988 | (#6) Kentucky vs. Maryland | W | 90 - 81 | NCAA Southwest Regional Second Round (at Cincinnati, OH) (win voided by probation) |
| 12/15/1958 | Maryland at (#2) Kentucky | W | 58 - 56 OT | - |
| 12/9/1957 | Kentucky at Maryland | L | 62 - 71 | - |
| 12/15/1956 | Maryland at (#3) Kentucky | W | 76 - 55 | - |
| 12/15/1955 | (#12) Kentucky at Maryland | W | 62 - 61 | - |
| 3/3/1931 | Kentucky vs. Maryland | L | 27 - 29 | Southern Conference Tournament Championship (at Atlanta, GA) |
| 2/28/1930 | Kentucky vs. Maryland | W | 26 - 21 | Southern Conference Tournament (at Atlanta, GA) |
| 1/19/1928 | Kentucky at Maryland | L | 7 - 37 | - |
