Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 20, 1999 | Meade County | away | W | 40–3 | 1-0 | ||
| Fri, Aug 27, 1999 | Greenwood | home | W | 27–22 | 2-0 | ||
| Fri, Sep 10, 1999 | Taylor County | home | L | 14–15 | 2-1 | ||
| Fri, Sep 17, 1999 | Fort Knox | home | W | 34–3 | 3-1 | District game | |
| Fri, Sep 24, 1999 | Moore | away | W | 29–12 | 4-1 | District game | |
| Fri, Oct 1, 1999 | Western | away | W | 52–7 | 5-1 | District game | |
| Fri, Oct 8, 1999 | Shawnee | home | W | 48–14 | 6-1 | District game | |
| Fri, Oct 15, 1999 | Elizabethtown | away | W | 35–21 | 7-1 | District game | |
| Fri, Oct 22, 1999 | Washington County | home | W | 26–6 | 8-1 | District game | |
| Sat, Oct 30, 1999 | DeSales | at iroquois hs | W | 20–7 | 9-1 | District game | |
| Fri, Nov 5, 1999 | Green County | home | W | 49–12 | 10-1 | Class AA Tournament First Round Class AA | |
| Fri, Nov 12, 1999 | Taylor County | home | L | 21–26 | 10-2 | Class AA Tournament Second Round Class AA |