Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Western Hills | at east/west grid classic, east jessamine hs | W | 34–14 | 1-0 | ||
| Fri, Aug 27, 1999 | Anderson County | away | W | 13–7 | 2-0 | ||
| Fri, Sep 3, 1999 | East Jessamine | home | W | 13–6 | 3-0 | ||
| Fri, Sep 10, 1999 | Rowan County | away | W | 40–16 | 4-0 | ||
| Fri, Sep 17, 1999 | Mercer County | away | L | 7–14 | 4-1 | District game | |
| Fri, Oct 1, 1999 | Henry County | home | W | 19–0 | 5-1 | District game | |
| Fri, Oct 8, 1999 | Boyle County | away | L | 6–42 | 5-2 | District game | |
| Fri, Oct 15, 1999 | Garrard County | home | L | 22–38 | 5-3 | District game | |
| Fri, Oct 22, 1999 | Owen County | away | W | 48–0 | 6-3 | District game | |
| Fri, Oct 29, 1999 | Lexington Catholic | home | L | 24–50 | 6-4 | District game |
