Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Millersburg Military | home | W | 55–14 | 1-0 | ||
| Fri, Sep 3, 1999 | Bath County | home | L | 6–32 | 1-1 | ||
| Fri, Sep 10, 1999 | Pike County Central | away | L | 12–54 | 1-2 | ||
| Fri, Sep 17, 1999 | Fairview | home | W | 46–21 | 2-2 | ||
| Fri, Sep 24, 1999 | Powell County | home | L | 22–55 | 2-3 | ||
| Fri, Oct 1, 1999 | Estill County | away | L | 0–50 | 2-4 | District game | |
| Fri, Oct 8, 1999 | Leslie County | away | L | 20–61 | 2-5 | District game | |
| Fri, Oct 15, 1999 | Breathitt County | home | L | 12–66 | 2-6 | District game | |
| Fri, Oct 22, 1999 | Powell County | away | L | 0–57 | 2-7 | District game | |
| Fri, Oct 29, 1999 | Middlesboro | home | L | 12–81 | 2-8 | District game |
