Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Mayfield | home | L | 0–14 | 0-1 | ||
| Fri, Sep 3, 1999 | Caldwell County | away | W | 42–0 | 1-1 | ||
| Fri, Sep 10, 1999 | Paducah Tilghman | away | W | 21–12 | 2-1 | ||
| Fri, Sep 17, 1999 | Paul Laurence Dunbar | at paul dunbar | L | 15–33 | 2-2 | ||
| Fri, Sep 24, 1999 | Hopkinsville | home | L | 13–30 | 2-3 | District game | |
| Fri, Oct 1, 1999 | Calloway County | away | W | 10–6 | 3-3 | ||
| Fri, Oct 8, 1999 | Madisonville-North Hopkins | away | L | 19–35 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Christian County | home | W | 61–22 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Henderson County | home | W | 28–7 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Graves County | home | W | 35–14 | 6-4 | District game | |
| Fri, Nov 5, 1999 | Greenwood | away | W | 34–14 | 7-4 | Class AAAA Tournament First Round Class AAAA | |
| Fri, Nov 12, 1999 | Hopkinsville | away | L | 21–35 | 7-5 | Class AAAA Tournament Second Round Class AA… |