| Date | H/A | W/L | Team | Score | Opponent | Score | ||
| 2023-08-25 | A | W | James Monroe | 45 | Wheeling Central (5) | 32 | Hx 411 | |
| 2023-09-08 | A | W | James Monroe | 54 | PikeView (0) | 8 | Hx 362 | |
| 2023-09-22 | A | W | James Monroe | 21 | Narrows (VA) (8) | 6 | Hx 532 | |
| 2023-09-29 | H | W | James Monroe | 50 | Summers County (6) | 26 | Hx 533 | |
| 2023-10-06 | A | L | James Monroe | 8 | Greenbrier West (13) | 25 | Hx 520 | |
| 2023-10-13 | H | W | James Monroe | 49 | Midland Trail (5) | 0 | Hx 534 | |
| 2023-10-20 | H | W | James Monroe | 35 | Liberty-Raleigh (2) | 0 | Hx 318 | |
| 2023-10-27 | A | W | James Monroe | 28 | Nicholas County (4) | 12 | Hx 343 | |
| 2023-11-03 | H | W | James Monroe | 35 | Bluefield (4) | 32 | Hx 227 | |
| 2023-11-11 | H | W | James Monroe | 48 | Sherman (6) | 15 | A 1st Round 1 vs 16 | Hx 1229 |
| 2023-11-18 | H | W | James Monroe | 17 | Cameron (10) | 0 | A Quarterfinals 1 vs 8 | Hx 1238 |
| 2023-11-24 | H | L | James Monroe | 7 | Greenbrier West (13) | 27 | A Semifinals 4 vs 1 | Hx 1246 |