Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Rockcastle County | at death valley bowl, lincoln county hs | L | 7–10 | 0-1 | ||
| Fri, Aug 27, 1999 | George Rogers Clark | home | W | 34–12 | 1-1 | ||
| Fri, Sep 3, 1999 | Harrodsburg | away | L | 21–25 | 1-2 | ||
| Fri, Sep 17, 1999 | Montgomery County | home | W | 43–21 | 2-2 | District game | |
| Fri, Sep 24, 1999 | Franklin County | away | L | 6–48 | 2-3 | District game | |
| Thu, Sep 30, 1999 | Western Hills | home | W | 27–12 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Grant County | away | W | 29–12 | 4-3 | District game | |
| Fri, Oct 15, 1999 | Anderson County | home | W | 40–22 | 5-3 | District game | |
| Fri, Oct 22, 1999 | Bourbon County | away | W | 22–13 | 6-3 | District game | |
| Fri, Oct 29, 1999 | Prestonsburg | home | W | 36–6 | 7-3 | ||
| Fri, Nov 5, 1999 | Covington Catholic | home | W | 21–16 | 8-3 | Class AAA Tournament First Round Class AAA | |
| Fri, Nov 12, 1999 | Highlands | away | L | 26–62 | 8-4 | Class AAA Tournament Second Round Class AAA |