Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Madison Central | at recreation bowl, montgomery county hs | L | 28–32 | 0-1 | ||
| Sat, Aug 28, 1999 | Lincoln County | at new image gridiron classic, rawlings stadium | W | 22–21 | 1-1 | ||
| Fri, Sep 3, 1999 | Paul Laurence Dunbar | home | L | 35–36 | 1-2 | (Overtime) | |
| Fri, Sep 10, 1999 | Woodford County | away | W | 50–0 | 2-2 | ||
| Fri, Sep 17, 1999 | Simon Kenton | home | W | 49–20 | 3-2 | District game | |
| Fri, Sep 24, 1999 | Boone County | away | L | 14–38 | 3-3 | District game | |
| Fri, Oct 1, 1999 | Bryan Station | away | L | 14–56 | 3-4 | District game | |
| Fri, Oct 8, 1999 | Campbell County | home | W | 47–28 | 4-4 | District game | |
| Fri, Oct 15, 1999 | Ryle | away | L | 20–35 | 4-5 | District game | |
| Fri, Oct 22, 1999 | Henry Clay | home | L | 28–57 | 4-6 | District game |