Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Franklin-Simpson | at constitution bowl, danville hs | L | 13–41 | 0-1 | ||
| Fri, Aug 27, 1999 | Hazard | away | W | 37–8 | 1-1 | ||
| Fri, Sep 3, 1999 | Boyle County | home | L | 3–28 | 1-2 | ||
| Fri, Sep 10, 1999 | Southwestern | at pulaski southwestern | L | 25–27 | 1-3 | ||
| Fri, Sep 17, 1999 | Woodford County | home | W | 63–15 | 2-3 | ||
| Fri, Sep 24, 1999 | Montgomery County | away | W | 47–21 | 3-3 | ||
| Fri, Oct 8, 1999 | Campbellsville | home | L | 14–27 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Harrodsburg | away | L | 22–28 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Somerset | home | W | 35–14 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Metcalfe County | away | W | 69–6 | 5-5 | District game | |
| Fri, Nov 5, 1999 | Carroll County | away | W | 49–6 | 6-5 | Class A Tournament First Round Class A | |
| Fri, Nov 12, 1999 | Harrodsburg | away | W | 14–7 | 7-5 | Class A Tournament Second Round Class A | |
| Fri, Nov 19, 1999 | Somerset | home | L | 0–10 | 7-6 | Class A Tournament Quarter Finals Class A |