Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Fleming County | home | W | 22–20 | 1-0 | ||
| Fri, Sep 3, 1999 | Raceland | home | W | 18–16 | 2-0 | ||
| Fri, Sep 10, 1999 | Fleming-Neon | home | W | 46–42 | 3-0 | District game | |
| Fri, Sep 17, 1999 | Elkhorn City | home | W | 65–22 | 4-0 | District game | |
| Fri, Sep 24, 1999 | Allen Central | away | W | 35–7 | 5-0 | ||
| Thu, Sep 30, 1999 | Johnson Central | away | L | 14–22 | 5-1 | ||
| Fri, Oct 8, 1999 | Phelps | away | W | 35–9 | 6-1 | District Game | |
| Fri, Oct 15, 1999 | Hazard | away | L | 0–33 | 6-2 | District game | |
| Fri, Oct 22, 1999 | South Floyd | home | W | 34–30 | 7-2 | District game | |
| Fri, Oct 29, 1999 | Pikeville | away | L | 11–49 | 7-3 | District game | |
| Fri, Nov 5, 1999 | Williamsburg | away | W | 61–6 | 8-3 | Class A Tournament First Round Class A | |
| Fri, Nov 12, 1999 | Pikeville | away | L | 15–41 | 8-4 | Class A Tournament Second Round Class A |
