Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Clay County | home | W | 20–19 | 1-0 | ||
| Fri, Sep 3, 1999 | Perry County Central | away | L | 18–27 | 1-1 | ||
| Fri, Sep 10, 1999 | Harlan | home | L | 27–41 | 1-2 | ||
| Fri, Sep 17, 1999 | Whitesburg | away | W | 33–32 | 2-2 | (Double Overtime) | |
| Fri, Sep 24, 1999 | Breathitt County | away | L | 20–35 | 2-3 | District game | |
| Fri, Oct 1, 1999 | Allen Central | home | W | 48–21 | 3-3 | ||
| Fri, Oct 8, 1999 | Morgan County | home | W | 61–20 | 4-3 | District game | |
| Fri, Oct 15, 1999 | Middlesboro | home | L | 12–21 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Estill County | away | W | 39–29 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Powell County | away | W | 49–34 | 6-4 | District game | |
| Fri, Nov 5, 1999 | Shelby Valley | away | W | 40–18 | 7-4 | Class AA Tournament First Round Class AA | |
| Fri, Nov 12, 1999 | Middlesboro | away | L | 20–43 | 7-5 | Class AA Tournament Second Round Class AA |
