Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Owensboro | away | L | 13–35 | 0-1 | ||
| Fri, Aug 27, 1999 | Evansville Bosse, IN | home | W | 54–26 | 1-1 | ||
| Fri, Sep 3, 1999 | Henderson County | away | W | 33–14 | 2-1 | ||
| Fri, Sep 10, 1999 | Owensboro Catholic | home | W | 28–10 | 3-1 | ||
| Fri, Sep 17, 1999 | Warren Central | home | W | 36–35 | 4-1 | ||
| Fri, Sep 24, 1999 | Apollo | home | L | 16–21 | 4-2 | District game | |
| Fri, Oct 1, 1999 | Ohio County | away | W | 20–19 | 5-2 | District game | |
| Fri, Oct 8, 1999 | Barren County | away | W | 54–8 | 6-2 | District game | |
| Fri, Oct 15, 1999 | Greenwood | home | L | 21–28 | 6-3 | District game | |
| Fri, Oct 22, 1999 | Grayson County | away | W | 41–9 | 7-3 | District game | |
| Sat, Nov 6, 1999 | Graves County | away | W | 26–25 | 8-3 | Class AAAA Tournament First Round Class AAAA | |
| Fri, Nov 12, 1999 | Madisonville-North Hopkins | home | L | 44–63 | 8-4 | Class AAAA Tournament Second Round Class AA… |