Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Eminence | away | L | 14–20 | 0-1 | ||
| Fri, Sep 3, 1999 | Owen County | home | W | 35–34 | 1-1 | ||
| Fri, Sep 17, 1999 | Kentucky Country Day | away | W | 28–22 | 2-1 | ||
| Sat, Sep 25, 1999 | Bethlehem | away | L | 6–13 | 2-2 | ||
| Fri, Oct 1, 1999 | Holy Cross (Louisville) | away | L | 7–35 | 2-3 | District game | |
| Fri, Oct 8, 1999 | Frankfort | home | L | 8–27 | 2-4 | District game | |
| Fri, Oct 15, 1999 | Carroll County | home | W | 30–22 | 3-4 | District game | |
| Fri, Oct 22, 1999 | Bardstown | away | L | 7–48 | 3-5 | District game | |
| Fri, Oct 29, 1999 | Christian Academy-Louisville | home | W | 64–0 | 4-5 | District game |
