Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | North Laurel | home | W | 14–0 | 1-0 | ||
| Fri, Sep 3, 1999 | Somerset | away | L | 26–43 | 1-1 | ||
| Fri, Sep 10, 1999 | Monroe County | away | W | 21–20 | 2-1 | ||
| Fri, Sep 17, 1999 | Harrodsburg | home | L | 7–21 | 2-2 | ||
| Fri, Sep 24, 1999 | Hart County | home | W | 32–26 | 3-2 | (Overtime) | |
| Thu, Sep 30, 1999 | Taylor County | away | L | 6–21 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Russell County | home | L | 20–41 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Green County | away | W | 21–20 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Casey County | home | W | 56–14 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Corbin | away | L | 21–35 | 5-5 | District game | |
| Fri, Nov 5, 1999 | Washington County | away | W | 14–12 | 6-5 | Class AA Tournament First Round Class AA | |
| Fri, Nov 12, 1999 | Corbin | away | L | 8–50 | 6-6 | Class AA Tournament Second Round Class AA |