| Date | H/A | W/L | Team | Score | Opponent | Score | ||
| 2021-08-27 | A | L | James Monroe | 8 | Sherman () | 19 | 535 | |
| 2021-09-17 | H | W | James Monroe | 50 | Meadow Bridge () | 12 | 537 | |
| 2021-09-21 | H | W | James Monroe | 12 | Pendleton County () | 7 | 536 | |
| 2021-10-01 | A | W | James Monroe | 62 | PikeView () | 14 | 353 | |
| 2021-10-08 | A | W | James Monroe | 20 | Greenbrier West () | 14 | 514 | |
| 2021-10-15 | H | W | James Monroe | 20 | Midland Trail () | 7 | 538 | |
| 2021-10-22 | H | L | James Monroe | 12 | Liberty-Raleigh () | 46 | 312 | |
| 2021-10-29 | A | L | James Monroe | 7 | Nicholas County () | 25 | 334 | |
| 2021-11-02 | A | W | James Monroe | 35 | Covington (VA) () | 16 | 411 | |
| 2021-11-05 | H | W | James Monroe | 32 | Summers County () | 6 | 539 | |
| 2021-11-13 | H | W | James Monroe | 32 | Trinity () | 0 | 7-10 1st RD | 1269 |
| 2021-11-20 | A | L | James Monroe | 0 | Doddridge County () | 14 | Quarterfinals | 1305 |