Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Harrison County | at death valley bowl, lincoln county hs | W | 10–7 | 1-0 | ||
| Fri, Aug 27, 1999 | South Laurel | home | W | 24–14 | 2-0 | ||
| Fri, Sep 3, 1999 | Southwestern | at pulaski southwestern | L | 13–42 | 2-1 | ||
| Fri, Sep 17, 1999 | Estill County | home | W | 34–0 | 3-1 | ||
| Fri, Sep 24, 1999 | Knott County Central | home | W | 55–0 | 4-1 | District game | |
| Fri, Oct 1, 1999 | North Laurel | away | W | 40–7 | 5-1 | ||
| Fri, Oct 8, 1999 | Whitley County | away | W | 21–20 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Knox Central | home | W | 55–0 | 7-1 | District game | |
| Fri, Oct 22, 1999 | Cawood | home | W | 63–6 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Bell County | away | L | 7–19 | 8-2 | District game | |
| Fri, Nov 5, 1999 | Greenup County | home | W | 29–15 | 9-2 | Class AAA Tournament First Round Class AAA | |
| Fri, Nov 12, 1999 | Sheldon Clark | away | W | 31–14 | 10-2 | Class AAA Tournament Second Round Class AAA | |
| Fri, Nov 19, 1999 | Lawrence County | home | L | 14–48 | 10-3 | Class AAA Tournament Quarter Finals Class A… |