| 9/7/2019 | Averett (7-3) | 28 | at | Hampden-Sydney | 16 | USASC | ||
| 9/14/2019 | Hampden-Sydney | 27 | at | Christopher Newport (2-8) | 24 | OT | at NJAC | |
| 9/21/2019 | Hampden-Sydney | 17 | at | Southern Virginia (4-6,2-6) | 29 | |||
| 9/28/2019 | Washington and Lee (6-4,5-3) | 43 | at | Hampden-Sydney | 24 | |||
| 10/5/2019 | Hampden-Sydney | 17 | at | Emory & Henry (7-3,6-2) | 56 | |||
| 10/12/2019 | Bridgewater VA (10-1,8-0) | 51 | at | Hampden-Sydney | 7 | |||
| 10/19/2019 | Shenandoah (6-4,4-4) | 21 | at | Hampden-Sydney | 17 | |||
| 10/26/2019 | Hampden-Sydney | 27 | at | Guilford (2-8,1-7) | 37 | |||
| 11/9/2019 | Ferrum (4-6,3-5) | 31 | at | Hampden-Sydney | 14 | |||
| 11/16/2019 | Hampden-Sydney | 3 | at | Randolph-Macon (9-2,7-1) | 45 |
| vs Hampden-Sydney | vs Other Opponents | Hampden-Sydney compared to OOs | |
| Record: | 9-1 | 48-44 | |
| Points Scored: | 36.50 | 28.78 | -7.72 |
| Points Allowed: | 16.90 | 26.18 | -9.28 |
| Margin: | 19.60 | 2.60 | -17.00 |
| Total Points: | 53.40 | 54.96 | -1.56 |