Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Grant County | at alumni bowl, whitley county hs | L | 0–8 | 0-1 | ||
| Fri, Aug 27, 1999 | Evarts | away | L | 0–6 | 0-2 | ||
| Fri, Sep 10, 1999 | Knott County Central | home | W | 26–13 | 1-2 | ||
| Fri, Sep 17, 1999 | Lincoln County | away | L | 8–41 | 1-3 | District game | |
| Fri, Sep 24, 1999 | Southwestern | home | L | 0–76 | 1-4 | District game | |
| Fri, Oct 1, 1999 | Adair County | away | W | 62–28 | 2-4 | District Games | |
| Fri, Oct 8, 1999 | Madison Southern | home | W | 36–16 | 3-4 | District game | |
| Fri, Oct 15, 1999 | East Jessamine | home | L | 22–42 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Pulaski County | away | W | 38–35 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Marion County | away | L | 8–47 | 4-6 | District game |
