Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Boyle County | away | L | 32–33 | 0-1 | ||
| Fri, Sep 3, 1999 | Rockcastle County | at pulaski southwestern | W | 42–13 | 1-1 | ||
| Fri, Sep 10, 1999 | Danville | at pulaski southwestern | W | 27–25 | 2-1 | ||
| Fri, Sep 17, 1999 | Adair County | away | W | 70–0 | 3-1 | District game | |
| Fri, Sep 24, 1999 | McCreary Central | away | W | 76–0 | 4-1 | District game | |
| Fri, Oct 1, 1999 | Madison Southern | away | W | 64–0 | 5-1 | District game | |
| Fri, Oct 8, 1999 | East Jessamine | at pulaski southwestern | W | 63–20 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Pulaski County | away | W | 61–7 | 7-1 | District game | |
| Fri, Oct 22, 1999 | Marion County | at pulaski southwestern | W | 69–26 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Lincoln County | at pulaski southwestern | W | 25–9 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Bullitt East | at pulaski southwestern | L | 15–19 | 9-2 | Class AAA Tournament First Round Class AAA |