Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | George Rogers Clark | away | W | 60–30 | 1-0 | ||
| Fri, Aug 27, 1999 | Rockcastle County | away | L | 14–24 | 1-1 | ||
| Fri, Sep 3, 1999 | Corbin | home | W | 35–20 | 2-1 | ||
| Fri, Sep 10, 1999 | North Laurel | away | W | 34–0 | 3-1 | District game | |
| Fri, Sep 17, 1999 | Cawood | away | W | 30–2 | 4-1 | ||
| Fri, Sep 24, 1999 | Lafayette | home | W | 55–14 | 5-1 | ||
| Fri, Oct 8, 1999 | Johnson Central | home | W | 59–30 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Perry County Central | away | W | 70–19 | 7-1 | District game | |
| Fri, Oct 22, 1999 | Boyd County | away | W | 57–42 | 8-1 | District game | |
| Fri, Oct 29, 1999 | Clay County | home | W | 46–6 | 9-1 | District game | |
| Fri, Nov 5, 1999 | George Rogers Clark | home | W | 55–2 | 10-1 | Class AAAA Tournament First Round Class AAAA | |
| Fri, Nov 12, 1999 | Madison Central | home | W | 58–53 | 11-1 | Class AAAA Tournament Second Round Class AA… | |
| Fri, Nov 19, 1999 | Tates Creek | away | L | 37–42 | 11-2 | Class AAAA Tournament Quarter Finals Class … |