Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Franklin County | at east/west grid classic, east jessamine hs | L | 7–32 | 0-1 | ||
| Fri, Sep 3, 1999 | West Jessamine | away | L | 6–13 | 0-2 | ||
| Fri, Sep 10, 1999 | Grant County | home | W | 21–20 | 1-2 | (Double Overtime) | |
| Fri, Sep 17, 1999 | Pulaski County | home | W | 6–0 | 2-2 | District game | |
| Fri, Sep 24, 1999 | Marion County | home | W | 15–14 | 3-2 | District game | |
| Thu, Sep 30, 1999 | Lincoln County | away | L | 12–25 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Southwestern | at pulaski southwestern | L | 20–63 | 3-4 | District game | |
| Fri, Oct 15, 1999 | McCreary Central | away | W | 42–22 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Madison Southern | home | W | 35–14 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Adair County | away | W | 28–21 | 6-4 | District game | |
| Fri, Nov 5, 1999 | Waggener | away | L | 13–35 | 6-5 | Class AAA Tournament First Round Class AAA |