| Date | H/A | W/L | Team | Score | Opponent | Score | ||
| 2021-08-27 | H | W | Woodrow Wilson | 39 | Riverside (3) | 12 | Hx 178 | |
| 2021-09-03 | H | L | Woodrow Wilson | 14 | Greenbrier East (6) | 28 | Hx 71 | |
| 2021-09-10 | A | L | Woodrow Wilson | 13 | Parkersburg South (5) | 61 | Hx 13 | |
| 2021-09-24 | H | W | Woodrow Wilson | 28 | Morgantown (5) | 27 | 1 OT Hx 140 | |
| 2021-10-01 | H | L | Woodrow Wilson | 14 | Princeton (4) | 21 | Hx 173 | |
| 2021-10-08 | A | L | Woodrow Wilson | 0 | Huntington (13) | 63 | Hx 99 | |
| 2021-10-22 | A | L | Woodrow Wilson | 35 | George Washington (8) | 48 | Hx 69 | |
| 2021-10-27 | H | W | Woodrow Wilson | 1 | Bluefield (7) | 0 | Hx 1256 | |
| 2021-10-29 | H | W | Woodrow Wilson | 49 | Oak Hill (2) | 10 | Hx 165 | |
| 2021-11-05 | A | W | Woodrow Wilson | 42 | South Charleston (5) | 21 | Hx 184 | |
| 2021-11-12 | A | L | Woodrow Wilson | 10 | University (10) | 52 | 4-13 1st RD | Hx 1282 |