| Date | H/A | W/L | Team | Score | Opponent | Score | ||
| 2021-08-27 | H | W | Woodrow Wilson | 39 | Riverside () | 12 | 178 | |
| 2021-09-03 | H | L | Woodrow Wilson | 14 | Greenbrier East () | 28 | 71 | |
| 2021-09-10 | A | L | Woodrow Wilson | 13 | Parkersburg South () | 61 | 13 | |
| 2021-09-24 | H | W | Woodrow Wilson | 28 | Morgantown () | 27 | 1 OT140 | |
| 2021-10-01 | H | L | Woodrow Wilson | 14 | Princeton () | 21 | 173 | |
| 2021-10-08 | A | L | Woodrow Wilson | 0 | Huntington () | 63 | 99 | |
| 2021-10-22 | A | L | Woodrow Wilson | 35 | George Washington () | 48 | 69 | |
| 2021-10-27 | H | W | Woodrow Wilson | 1 | Bluefield () | 0 | 1256 | |
| 2021-10-29 | H | W | Woodrow Wilson | 49 | Oak Hill () | 10 | 165 | |
| 2021-11-05 | A | W | Woodrow Wilson | 42 | South Charleston () | 21 | 184 | |
| 2021-11-12 | A | L | Woodrow Wilson | 10 | University () | 52 | 4-13 1st RD | 1282 |