| Date | H/A | W/L | Team | Score | Opponent | Score | ||
| 2023-08-25 | H | W | Woodrow Wilson | 38 | Riverside (2) | 13 | Hx 179 | |
| 2023-09-01 | H | W | Woodrow Wilson | 42 | Greenbrier East (2) | 39 | Hx 81 | |
| 2023-09-08 | A | L | Woodrow Wilson | 20 | Parkersburg South (6) | 56 | Hx 18 | |
| 2023-09-16 | A | W | Woodrow Wilson | 28 | Bluefield (4) | 27 | Hx 203 | |
| 2023-09-22 | H | W | Woodrow Wilson | 49 | Lincoln County (2) | 21 | Hx 135 | |
| 2023-09-28 | A | W | Woodrow Wilson | 50 | Preston (1) | 13 | Hx 167 | |
| 2023-10-06 | A | L | Woodrow Wilson | 0 | Huntington (11) | 49 | Hx 108 | |
| 2023-10-13 | A | L | Woodrow Wilson | 20 | Princeton (10) | 55 | Hx 173 | |
| 2023-10-27 | H | L | Woodrow Wilson | 19 | Oak Hill (5) | 21 | Hx 155 | |
| 2023-11-03 | A | L | Woodrow Wilson | 8 | George Washington (6) | 62 | Hx 68 |