Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Sat, Aug 21, 1999 | Scott County | at recreation bowl, montgomery county hs | W | 32–28 | 1-0 | ||
| Sat, Aug 28, 1999 | Trinity (Louisville) | at comair bowl, ryle hs | L | 16–39 | 1-1 | ||
| Fri, Sep 3, 1999 | Oldham County | away | W | 27–20 | 2-1 | ||
| Fri, Sep 10, 1999 | Lexington Catholic | home | L | 26–70 | 2-2 | ||
| Fri, Sep 24, 1999 | Scott | home | W | 47–9 | 3-2 | ||
| Thu, Sep 30, 1999 | Woodford County | home | W | 67–0 | 4-2 | District game | |
| Fri, Oct 8, 1999 | Tates Creek | away | W | 42–19 | 5-2 | District game | |
| Fri, Oct 15, 1999 | Lafayette | away | W | 61–33 | 6-2 | District game | |
| Fri, Oct 22, 1999 | George Rogers Clark | home | W | 40–20 | 7-2 | District game | |
| Fri, Oct 29, 1999 | Paul Laurence Dunbar | at paul dunbar | L | 35–63 | 7-3 | District game | |
| Fri, Nov 5, 1999 | Johnson Central | home | W | 63–55 | 8-3 | Class AAAA Tournament First Round Class AAA… | |
| Fri, Nov 12, 1999 | South Laurel | away | L | 53–58 | 8-4 | Class AAAA Tournament Second Round Class AA… |