Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Betsy Layne | away | W | 14–6 | 1-0 | ||
| Sat, Aug 28, 1999 | Berea | at craft bowl, madison southern hs | W | 14–8 | 2-0 | ||
| Fri, Sep 3, 1999 | Casey County | away | L | 14–15 | 2-1 | ||
| Fri, Sep 10, 1999 | Bethlehem | home | L | 28–34 | 2-2 | ||
| Fri, Sep 24, 1999 | Morgan County | away | W | 55–22 | 3-2 | ||
| Fri, Oct 1, 1999 | Middlesboro | away | L | 9–56 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Breathitt County | home | L | 7–68 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Estill County | away | L | 7–48 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Morgan County | home | W | 57–0 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Leslie County | home | L | 34–49 | 4-6 | District game |