Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Kentucky Country Day | away | W | 20–12 | 1-0 | ||
| Fri, Sep 3, 1999 | Shawnee | home | W | 35–0 | 2-0 | ||
| Fri, Sep 10, 1999 | Owen County | away | W | 35–0 | 3-0 | ||
| Fri, Sep 17, 1999 | Bethlehem | home | W | 42–0 | 4-0 | ||
| Fri, Sep 24, 1999 | Eminence | home | L | 14–20 | 4-1 | ||
| Fri, Oct 1, 1999 | Frankfort | away | W | 21–0 | 5-1 | District game | |
| Fri, Oct 8, 1999 | Christian Academy-Louisville | home | W | 49–12 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Trimble County | away | L | 22–30 | 6-2 | District game | |
| Fri, Oct 22, 1999 | Holy Cross (Louisville) | home | W | 28–14 | 7-2 | District game | |
| Fri, Oct 29, 1999 | Bardstown | away | L | 8–56 | 7-3 | District game | |
| Fri, Nov 5, 1999 | Danville | home | L | 6–49 | 7-4 | Class A Tournament First Round Class A |
