Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Warren East | away | W | 52–6 | 1-0 | ||
| Fri, Aug 27, 1999 | Allen County-Scottsville | away | L | 0–14 | 1-1 | ||
| Fri, Sep 10, 1999 | Wayne County | home | L | 20–21 | 1-2 | ||
| Fri, Sep 17, 1999 | Barren County | home | W | 14–7 | 2-2 | ||
| Fri, Sep 24, 1999 | Taylor County | away | L | 7–24 | 2-3 | ||
| Thu, Sep 30, 1999 | Hart County | home | W | 36–14 | 3-3 | District game | |
| Fri, Oct 8, 1999 | Owensboro Catholic | away | L | 0–17 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Butler County | home | W | 40–6 | 4-4 | District game | |
| Fri, Oct 22, 1999 | Edmonson County | away | W | 7–3 | 5-4 | District game | |
| Fri, Oct 29, 1999 | Glasgow | home | L | 6–36 | 5-5 | District game | |
| Fri, Nov 5, 1999 | McLean County | away | W | 36–7 | 6-5 | Class AA Tournament First Round Class AA | |
| Sat, Nov 13, 1999 | Owensboro Catholic | away | L | 3–14 | 6-6 | Class AA Tournament Second Round Class AA |