Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Montgomery County | at recreation bowl, montgomery county hs | W | 42–15 | 1-0 | ||
| Fri, Aug 27, 1999 | Whitesburg | at hazard grid classic, hazard hs | W | 57–12 | 2-0 | ||
| Fri, Sep 3, 1999 | Cawood | home | W | 36–21 | 3-0 | ||
| Fri, Sep 10, 1999 | Clay County | home | W | 41–14 | 4-0 | ||
| Fri, Sep 24, 1999 | Leslie County | home | W | 35–20 | 5-0 | District game | |
| Fri, Oct 1, 1999 | Perry County Central | away | W | 36–31 | 6-0 | ||
| Fri, Oct 8, 1999 | Powell County | away | W | 68–7 | 7-0 | District game | |
| Fri, Oct 15, 1999 | Morgan County | away | W | 66–12 | 8-0 | District game | |
| Fri, Oct 22, 1999 | Middlesboro | away | L | 41–42 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Estill County | home | W | 42–14 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Prestonsburg | home | W | 55–12 | 10-1 | Class AA Tournament First Round Class AA | |
| Fri, Nov 12, 1999 | Belfry | away | W | 47–42 | 11-1 | Class AA Tournament Second Round Class AA | |
| Fri, Nov 19, 1999 | Middlesboro | away | L | 37–44 | 11-2 | Class AA Tournament Quarter Finals Class AA |