Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Dec 3, 1999 | North Laurel | away | L | 60–66 | 0-1 | ||
| Sat, Dec 4, 1999 | LaRue County | at campbellsville | W | 48–44 | 1-1 | Campbellsville Tip-Off Classic | |
| Tue, Dec 7, 1999 | Burgin | home | W | 60–39 | 2-1 | ||
| Fri, Dec 10, 1999 | Danville | home | W | 56–36 | 3-1 | ||
| Tue, Dec 14, 1999 | Mercer County | home | W | 65–38 | 4-1 | ||
| Fri, Dec 17, 1999 | Madison Southern | home | W | 49–39 | 5-1 | ||
| Mon, Dec 27, 1999 | Bryan Station | at berea | W | 55–49 | 6-1 | Berea Invitational | |
| Tue, Dec 28, 1999 | West Jessamine | at berea | W | 72–63 | 7-1 | Berea Invitational | |
| Wed, Dec 29, 1999 | Mercer County | at berea | W | 69–62 | 8-1 | Berea Invitational | |
| Thu, Dec 30, 1999 | Paul Laurence Dunbar | at berea | L | 37–58 | 8-2 | Berea Invitational (championship) | |
| Tue, Jan 4, 2000 | Lincoln County | home | W | 49–46 | 9-2 | ||
| Tue, Jan 11, 2000 | Model | home | W | 70–52 | 10-2 | ||
| Fri, Jan 14, 2000 | Harrodsburg | away | W | 57–48 | 11-2 | ||
| Mon, Jan 17, 2000 | Burgin | away | W | 54–43 | 12-2 | All A Classic (12th Region) | |
| Tue, Jan 18, 2000 | Southwestern | home | (postponed due to snow) | ||||
| Fri, Jan 21, 2000 | Harrodsburg | away | L | 48–53 | 12-3 | All A Classic (12th Region) | |
| Tue, Jan 25, 2000 | Jackson County | home | W | 60–30 | 13-3 | ||
| Tue, Feb 1, 2000 | Burgin | away | W | 63–49 | 14-3 | ||
| Fri, Feb 4, 2000 | Mercer County | away | W | 65–55 | 15-3 | ||
| Sat, Feb 5, 2000 | Clay County | away | L | 61–67 | 15-4 | ||
| Tue, Feb 8, 2000 | Harrodsburg | home | W | 47–45 | 16-4 | (overtime) | |
| Fri, Feb 11, 2000 | Boyle County | home | W | 55–51 | 17-4 | (overtime) | |
| Tue, Feb 15, 2000 | Estill County | home | W | 69–65 | 18-4 | ||
| Thu, Feb 17, 2000 | Southwestern | home | L | 53–56 | 18-5 | ||
| Fri, Feb 18, 2000 | McCreary Central | away | L | 54–60 | 18-6 | ||
| Tue, Feb 22, 2000 | Lexington Christian | home | W | 61–49 | 19-6 | ||
| Fri, Feb 25, 2000 | East Jessamine | away | L | 36–48 | 19-7 | ||
| Mon, Feb 28, 2000 | Mercer County | away | L | 51–57 | 19-8 | 46th District 46th District Tournament |