Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Hazard | away | W | 28–22 | 1-0 | ||
| Fri, Sep 3, 1999 | Knox Central | home | W | 34–13 | 2-0 | ||
| Fri, Sep 10, 1999 | Thomas Walker, VA | away | W | 38–12 | 3-0 | ||
| Fri, Sep 17, 1999 | Berea | home | L | 40–41 | 3-1 | ||
| Fri, Sep 24, 1999 | Middlesboro | home | L | 29–45 | 3-2 | ||
| Fri, Oct 1, 1999 | Williamsburg | away | L | 6–8 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Cumberland | home | W | 64–0 | 4-3 | District game | |
| Fri, Oct 15, 1999 | Lynn Camp | away | L | 6–27 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Harlan | home | L | 14–23 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Evarts | away | W | 50–20 | 5-5 | District game | |
| Fri, Nov 5, 1999 | Pikeville | away | L | 14–66 | 5-6 | Class A Tournament First Round Class A |
