Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Elkhorn City | at pike county bowl, pikeville hs | W | 46–12 | 1-0 | ||
| Sat, Aug 28, 1999 | South Floyd | home | W | 41–12 | 2-0 | ||
| Fri, Sep 3, 1999 | Knott County Central | away | W | 38–11 | 3-0 | ||
| Fri, Sep 10, 1999 | Magoffin County | away | W | 14–6 | 4-0 | ||
| Fri, Sep 17, 1999 | Pike County Central | home | W | 27–6 | 5-0 | District game | |
| Fri, Sep 24, 1999 | Williamson, WV | home | W | 22–21 | 6-0 | (Overtime) | |
| Fri, Oct 8, 1999 | Whitesburg | home | W | 47–7 | 7-0 | District game | |
| Fri, Oct 15, 1999 | Betsy Layne | home | W | 61–6 | 8-0 | District game | |
| Fri, Oct 22, 1999 | Prestonsburg | away | W | 20–14 | 9-0 | District game | |
| Fri, Oct 29, 1999 | Belfry | home | L | 6–28 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Leslie County | home | L | 18–40 | 9-2 | Class AA Tournament First Round Class AA |