Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Boyle County | at pike county bowl, pikeville hs | L | 6–24 | 0-1 | ||
| Fri, Aug 27, 1999 | Prestonsburg | home | W | 39–0 | 1-1 | ||
| Fri, Sep 3, 1999 | Elkhorn City | home | W | 73–6 | 2-1 | District game | |
| Fri, Sep 10, 1999 | Hazard | away | W | 56–20 | 3-1 | District game | |
| Fri, Sep 17, 1999 | South Floyd | away | W | 47–22 | 4-1 | District game | |
| Fri, Sep 24, 1999 | Belfry | away | W | 26–8 | 5-1 | ||
| Thu, Sep 30, 1999 | Phelps | away | W | 48–0 | 6-1 | District game | |
| Sat, Oct 9, 1999 | Jenkins | home | W | 74–0 | 7-1 | ||
| Fri, Oct 15, 1999 | Fleming-Neon | home | W | 58–6 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Paintsville | home | W | 49–11 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Pineville | home | W | 66–14 | 10-1 | Class A Tournament First Round Class A | |
| Fri, Nov 12, 1999 | Paintsville | home | W | 41–15 | 11-1 | Class A Tournament Second Round Class A | |
| Fri, Nov 19, 1999 | Harlan | away | W | 33–12 | 12-1 | Class A Tournament Quarter Finals Class A | |
| Fri, Nov 26, 1999 | Beechwood | away | L | 19–25 | 12-2 | Class A Tournament Semi Finals Class A |