Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Shelby Valley | at pike county bowl, pikeville hs | L | 12–46 | 0-1 | ||
| Fri, Aug 27, 1999 | Cumberland | home | W | 44–38 | 1-1 | ||
| Fri, Sep 3, 1999 | Pikeville | away | L | 6–73 | 1-2 | District game | |
| Fri, Sep 10, 1999 | Jenkins | away | W | 33–12 | 2-2 | ||
| Fri, Sep 17, 1999 | Paintsville | away | L | 22–65 | 2-3 | District game | |
| Fri, Sep 24, 1999 | Evarts | home | L | 6–45 | 2-4 | ||
| Fri, Oct 8, 1999 | Fleming-Neon | away | L | 20–47 | 2-5 | District game | |
| Fri, Oct 15, 1999 | Phelps | home | W | 15–7 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Hazard | home | L | 6–41 | 3-6 | District game | |
| Fri, Oct 29, 1999 | South Floyd | away | L | 16–66 | 3-7 | District game |
