Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Henry Clay | away | L | 14–42 | 0-1 | ||
| Sat, Aug 28, 1999 | Bell County | away | W | 29–13 | 1-1 | ||
| Fri, Sep 3, 1999 | Bryan Station | away | W | 26–21 | 2-1 | ||
| Fri, Sep 10, 1999 | Johnson Central | away | W | 27–15 | 3-1 | ||
| Fri, Sep 24, 1999 | Dixie Heights | home | W | 27–21 | 4-1 | ||
| Fri, Oct 1, 1999 | Paul Laurence Dunbar | at paul dunbar | W | 36–19 | 5-1 | District game | |
| Fri, Oct 8, 1999 | Madison Central | home | L | 19–42 | 5-2 | District game | |
| Fri, Oct 15, 1999 | George Rogers Clark | home | W | 59–7 | 6-2 | District game | |
| Fri, Oct 22, 1999 | Woodford County | away | W | 61–8 | 7-2 | District game | |
| Fri, Oct 29, 1999 | Lafayette | home | W | 43–20 | 8-2 | District game | |
| Fri, Nov 5, 1999 | Perry County Central | home | W | 51–10 | 9-2 | Class AAAA Tournament First Round Class AAAA | |
| Fri, Nov 12, 1999 | Paul Laurence Dunbar | home | W | 49–36 | 10-2 | Class AAAA Tournament Second Round Class AA… | |
| Fri, Nov 19, 1999 | South Laurel | home | W | 42–37 | 11-2 | Class AAAA Tournament Quarter Finals Class … | |
| Fri, Nov 26, 1999 | Bryan Station | away | L | 16–55 | 11-3 | Class AAAA Tournament Semi Finals Class AAAA |