| 9/4/2021 | Baldwin-Wallace (8-2) | 45 | at | Hampden-Sydney | 24 | OAC | ||
| 9/11/2021 | Hampden-Sydney | 27 | at | Widener (7-4) | 34 | at MidAC | ||
| 9/18/2021 | Shenandoah (7-3,3-3) | 7 | at | Hampden-Sydney | 28 | |||
| 9/25/2021 | Hampden-Sydney | 28 | at | Guilford (1-7,0-6) | 27 | |||
| 10/2/2021 | Washington and Lee (8-3,5-1) | 32 | at | Hampden-Sydney | 30 | |||
| 10/16/2021 | Hampden-Sydney | 13 | at | Emory & Henry (6-4) | 37 | at D2Ind | ||
| 10/23/2021 | Ferrum (6-4,4-3) | 28 | at | Hampden-Sydney | 42 | |||
| 10/30/2021 | Hampden-Sydney | 38 | at | Apprentice (1-7) | 21 | at None | ||
| 11/6/2021 | Bridgewater VA (4-6,2-5) | 14 | at | Hampden-Sydney | 24 | |||
| 11/13/2021 | Hampden-Sydney | 14 | at | Randolph-Macon (9-1,5-1) | 37 |
| vs Hampden-Sydney | vs Other Opponents | Hampden-Sydney compared to OOs | |
| Record: | 5-5 | 52-36 | |
| Points Scored: | 28.20 | 27.35 | -0.85 |
| Points Allowed: | 26.80 | 23.45 | 3.35 |
| Margin: | 1.40 | 3.90 | 2.50 |
| Total Points: | 55.00 | 50.80 | 4.20 |