Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Nicholas County | away | L | 0–36 | 0-1 | ||
| Fri, Aug 27, 1999 | Estill County | home | L | 20–29 | 0-2 | ||
| Fri, Sep 3, 1999 | Morgan County | away | W | 32–6 | 1-2 | ||
| Fri, Sep 17, 1999 | Lewis County | home | W | 28–26 | 2-2 | ||
| Fri, Sep 24, 1999 | Mason County | home | L | 6–48 | 2-3 | District game | |
| Thu, Sep 30, 1999 | West Carter | away | W | 28–14 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Fleming County | home | L | 6–12 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Russell | away | L | 12–45 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Newport | away | L | 6–69 | 3-6 | District game | |
| Fri, Oct 29, 1999 | Lloyd Memorial | home | W | 20–14 | 4-6 | District game |
