Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | West Jessamine | at east/west grid classic, east jessamine hs | L | 14–34 | 0-1 | ||
| Fri, Sep 3, 1999 | Shelby County | home | W | 40–6 | 1-1 | ||
| Fri, Sep 10, 1999 | Campbellsville | home | L | 7–8 | 1-2 | ||
| Fri, Sep 17, 1999 | Anderson County | away | L | 26–32 | 1-3 | District game (Overtime) | |
| Fri, Sep 24, 1999 | Bourbon County | home | W | 27–6 | 2-3 | District game | |
| Thu, Sep 30, 1999 | Harrison County | away | L | 12–27 | 2-4 | District game | |
| Fri, Oct 8, 1999 | Montgomery County | home | L | 21–28 | 2-5 | District game | |
| Fri, Oct 15, 1999 | Franklin County | away | L | 21–49 | 2-6 | District game | |
| Fri, Oct 22, 1999 | Paris | away | W | 22–18 | 3-6 | ||
| Fri, Oct 29, 1999 | Grant County | home | L | 20–33 | 3-7 | District game |
