| Date | Opponent | Score |
|---|---|---|
| Sep 3, 1999 | Dewey | W, 41-13 |
| Sep 10, 1999 | Vinita | W, 24-18 |
| Sep 17, 1999 | at Pawhuska | W, 26-6 |
| Sep 24, 1999 | at Chelsea | W, 48-12 |
| Oct 1, 1999 | at Metro Christian | W, 29-0 |
| Oct 8, 1999 | Newkirk | W, 36-6 |
| Oct 15, 1999 | at Pawnee | W, 42-6 |
| Oct 21, 1999 | at Hominy | W, 43-24 |
| Oct 29, 1999 | Sperry | W, 42-14 |
| Nov 5, 1999 | Caney Valley | W, 60-6 |
| Nov 12, 1999 | at Stroud* | W, 41-0 |
| Nov 19, 1999 | at Wilburton* | W, 35-6 |
| Nov 26, 1999 | at Wewoka* | W, 31-20 |
| Dec 4, 1999 | at Davis* | W, 19-18 |
| Dec 11, 1999 | at Fairview* | L, 14-39 |
| * - Playoffs | ||