Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Simon Kenton | away | L | 11–38 | 0-1 | ||
| Fri, Sep 3, 1999 | Anderson County | at governor's bowl, woodford county hs | L | 19–28 | 0-2 | ||
| Fri, Sep 10, 1999 | Scott County | home | L | 0–50 | 0-3 | ||
| Fri, Sep 17, 1999 | Danville | away | L | 15–63 | 0-4 | ||
| Fri, Sep 24, 1999 | Holmes | home | L | 17–42 | 0-5 | ||
| Thu, Sep 30, 1999 | Madison Central | away | L | 0–67 | 0-6 | District game | |
| Fri, Oct 8, 1999 | Lafayette | home | L | 7–38 | 0-7 | District game | |
| Fri, Oct 15, 1999 | Paul Laurence Dunbar | at paul dunbar | L | 7–56 | 0-8 | District game | |
| Fri, Oct 22, 1999 | Tates Creek | home | L | 8–61 | 0-9 | District game | |
| Fri, Oct 29, 1999 | George Rogers Clark | away | L | 20–35 | 0-10 | District game |