Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Union County | away | L | 16–33 | 0-1 | ||
| Fri, Sep 3, 1999 | Owensboro Catholic | away | L | 19–29 | 0-2 | ||
| Fri, Sep 10, 1999 | Grayson County | home | W | 48–0 | 1-2 | District game | |
| Fri, Sep 17, 1999 | Owensboro | home | L | 14–26 | 1-3 | ||
| Fri, Sep 24, 1999 | Daviess County | away | W | 21–16 | 2-3 | District game | |
| Fri, Oct 1, 1999 | Greenwood | away | W | 27–0 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Hancock County | home | L | 7–39 | 3-4 | ||
| Fri, Oct 15, 1999 | Henderson County | home | W | 22–9 | 4-4 | ||
| Fri, Oct 22, 1999 | Ohio County | home | W | 32–6 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Barren County | home | W | 35–6 | 6-4 | District game | |
| Fri, Nov 5, 1999 | Madisonville-North Hopkins | home | L | 10–14 | 6-5 | Class AAAA Tournament First Round Class AAAA |
