Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Campbellsville | away | L | 0–30 | 0-1 | ||
| Fri, Aug 27, 1999 | Cawood | home | W | 19–0 | 1-1 | ||
| Fri, Sep 3, 1999 | Whitley County | home | L | 6–26 | 1-2 | ||
| Fri, Sep 10, 1999 | Ludlow | away | L | 8–10 | 1-3 | ||
| Fri, Sep 17, 1999 | Middlesboro | home | L | 21–34 | 1-4 | ||
| Fri, Oct 1, 1999 | Harlan | away | L | 27–28 | 1-5 | District game | |
| Fri, Oct 8, 1999 | Evarts | home | W | 54–14 | 2-5 | District game | |
| Fri, Oct 15, 1999 | Pineville | home | W | 27–6 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Cumberland | away | W | 41–6 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Williamsburg | away | L | 14–22 | 4-6 | District game | |
| Fri, Nov 5, 1999 | Hazard | away | W | 23–7 | 5-6 | Class A Tournament First Round Class A | |
| Fri, Nov 12, 1999 | Harlan | away | L | 14–20 | 5-7 | Class A Tournament Second Round Class A |
