Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Somerset | at pine montain classic, whitesburg hs | L | 7–24 | 0-1 | ||
| Fri, Aug 27, 1999 | Breathitt County | at hazard grid classic, hazard hs | L | 12–57 | 0-2 | ||
| Fri, Sep 10, 1999 | Perry County Central | away | L | 12–14 | 0-3 | ||
| Fri, Sep 17, 1999 | Leslie County | home | L | 32–33 | 0-4 | (Double Overtime) | |
| Fri, Sep 24, 1999 | Prestonsburg | home | L | 14–26 | 0-5 | District game | |
| Fri, Oct 1, 1999 | Fleming-Neon | home | W | 23–6 | 1-5 | ||
| Fri, Oct 8, 1999 | Shelby Valley | away | L | 7–47 | 1-6 | District game | |
| Fri, Oct 15, 1999 | Belfry | away | L | 0–39 | 1-7 | District game | |
| Fri, Oct 22, 1999 | Betsy Layne | away | W | 42–20 | 2-7 | District game | |
| Fri, Oct 29, 1999 | Pike County Central | home | W | 13–7 | 3-7 | District game (double overtime) | |
| Fri, Nov 5, 1999 | Middlesboro | away | L | 0–41 | 3-8 | Class AA Tournament First Round Class AA |