Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Magoffin County | home | W | 27–6 | 1-0 | ||
| Fri, Aug 27, 1999 | Bath County | away | W | 29–20 | 2-0 | ||
| Fri, Sep 3, 1999 | Madison Southern | home | W | 47–24 | 3-0 | ||
| Fri, Sep 10, 1999 | Mercer County | away | L | 7–49 | 3-1 | ||
| Fri, Sep 17, 1999 | Rockcastle County | away | L | 0–34 | 3-2 | ||
| Fri, Oct 1, 1999 | Morgan County | home | W | 50–0 | 4-2 | District game | |
| Fri, Oct 8, 1999 | Middlesboro | away | L | 64–69 | 4-3 | District game | |
| Fri, Oct 15, 1999 | Powell County | home | W | 48–7 | 5-3 | District game | |
| Fri, Oct 22, 1999 | Leslie County | home | L | 29–39 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Breathitt County | away | L | 14–42 | 5-5 | District game | |
| Fri, Nov 5, 1999 | Belfry | away | L | 12–62 | 5-6 | Class AA Tournament First Round Class AA |
