Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Allen Central | away | W | 34–26 | 1-0 | ||
| Fri, Aug 27, 1999 | Shawnee | away | L | 14–20 | 1-1 | ||
| Fri, Sep 3, 1999 | Kentucky Country Day | home | L | 26–27 | 1-2 | ||
| Fri, Sep 10, 1999 | Millersburg Military | home | W | 28–0 | 2-2 | ||
| Fri, Sep 24, 1999 | Berea | home | L | 6–8 | 2-3 | ||
| Fri, Oct 1, 1999 | Carroll County | home | L | 0–21 | 2-4 | District game | |
| Fri, Oct 8, 1999 | Trimble County | away | W | 27–8 | 3-4 | District game | |
| Fri, Oct 15, 1999 | Bardstown | home | L | 9–67 | 3-5 | District game | |
| Sat, Oct 23, 1999 | Christian Academy-Louisville | away | W | 22–16 | 4-5 | District game | |
| Fri, Oct 29, 1999 | Holy Cross (Louisville) | away | W | 10–7 | 5-5 | District game | |
| Fri, Nov 5, 1999 | Campbellsville | away | L | 0–48 | 5-6 | Class A Tournament First Round Class A |
