12 Games
| G | Date | Day | School | Opponent | Conf | Pts | Opp | W | L | Streak | Notes | ||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | Sep 4, 1999 | Sat | Kentucky | Louisville | CUSA | L | 28 | 56 | 0 | 1 | L 1 | ||
| 2 | Sep 11, 1999 | Sat | Kentucky | Connecticut | Non-Major | W | 45 | 14 | 1 | 1 | W 1 | ||
| 3 | Sep 18, 1999 | Sat | Kentucky | @ | Indiana | Big Ten | W | 44 | 35 | 2 | 1 | W 2 | |
| 4 | Sep 25, 1999 | Sat | Kentucky | (3) Florida | SEC | L | 10 | 38 | 2 | 2 | L 1 | ||
| 5 | Oct 2, 1999 | Sat | Kentucky | (20) Arkansas | SEC | W | 31 | 20 | 3 | 2 | W 1 | ||
| 6 | Oct 9, 1999 | Sat | Kentucky | @ | South Carolina | SEC | W | 30 | 10 | 4 | 2 | W 2 | |
| 7 | Oct 16, 1999 | Sat | Kentucky | LSU | SEC | W | 31 | 5 | 5 | 2 | W 3 | ||
| 8 | Oct 23, 1999 | Sat | Kentucky | @ | (14) Georgia | SEC | L | 34 | 49 | 5 | 3 | L 1 | |
| 9 | Nov 4, 1999 | Thu | Kentucky | @ | (8) Mississippi State | SEC | L | 22 | 23 | 5 | 4 | L 2 | |
| 10 | Nov 13, 1999 | Sat | Kentucky | @ | Vanderbilt | SEC | W | 19 | 17 | 6 | 4 | W 1 | |
| 11 | Nov 20, 1999 | Sat | Kentucky | (7) Tennessee | SEC | L | 21 | 56 | 6 | 5 | L 1 | ||
| 12 | Dec 29, 1999 | Wed | Kentucky | N | Syracuse | Big East | L | 13 | 20 | 6 | 6 | L 2 | Music City Bowl (Nashville, TN) |


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