Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Bourbon County | home | W | 20–13 | 1-0 | ||
| Fri, Aug 27, 1999 | Butler County | away | W | 41–0 | 2-0 | ||
| Fri, Sep 3, 1999 | Washington County | home | W | 12–0 | 3-0 | ||
| Fri, Sep 10, 1999 | Nelson County | away | L | 14–42 | 3-1 | ||
| Fri, Sep 17, 1999 | Glasgow | away | W | 27–24 | 4-1 | ||
| Sat, Oct 2, 1999 | Christian Academy-Louisville | away | W | 43–0 | 5-1 | District game | |
| Fri, Oct 8, 1999 | Holy Cross (Louisville) | home | W | 58–21 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Frankfort | away | W | 67–9 | 7-1 | District game | |
| Fri, Oct 22, 1999 | Trimble County | home | W | 48–7 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Carroll County | home | W | 56–8 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Somerset | home | L | 25–28 | 9-2 | Class A Tournament First Round Class A |