Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | McCreary Central | at alumni bowl, whitley county hs | W | 8–0 | 1-0 | ||
| Sat, Aug 28, 1999 | Garrard County | home | L | 12–45 | 1-1 | ||
| Sat, Sep 4, 1999 | Logan County | home | L | 25–41 | 1-2 | ||
| Fri, Sep 10, 1999 | East Jessamine | away | L | 20–21 | 1-3 | (Double Overtime) | |
| Fri, Sep 24, 1999 | Anderson County | home | L | 7–34 | 1-4 | District game | |
| Fri, Oct 1, 1999 | Bourbon County | away | L | 7–22 | 1-5 | District game | |
| Fri, Oct 8, 1999 | Harrison County | home | L | 12–29 | 1-6 | District game | |
| Fri, Oct 15, 1999 | Montgomery County | away | W | 47–27 | 2-6 | District game | |
| Fri, Oct 22, 1999 | Franklin County | home | L | 2–18 | 2-7 | District game | |
| Fri, Oct 29, 1999 | Western Hills | away | W | 33–20 | 3-7 | District game |
