Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Knox Central | home | W | 40–14 | 1-0 | ||
| Fri, Aug 27, 1999 | Leslie County | away | L | 19–20 | 1-1 | ||
| Fri, Sep 3, 1999 | Pulaski County | home | W | 35–0 | 2-1 | ||
| Fri, Sep 10, 1999 | Breathitt County | away | L | 14–41 | 2-2 | ||
| Fri, Sep 17, 1999 | George Rogers Clark | home | L | 6–16 | 2-3 | ||
| Fri, Oct 1, 1999 | Boyd County | home | L | 6–42 | 2-4 | District game | |
| Fri, Oct 8, 1999 | North Laurel | home | W | 30–27 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Johnson Central | away | L | 20–49 | 3-5 | District game | |
| Fri, Oct 22, 1999 | Perry County Central | home | L | 18–32 | 3-6 | District game | |
| Fri, Oct 29, 1999 | South Laurel | away | L | 6–46 | 3-7 | District game |
