| 9/7/2019 | Michigan Tech (5-5) | 29 | at | Hillsdale | 14 | GLIAC | ||
| 9/14/2019 | Hillsdale | 21 | at | Indianapolis (9-2) | 48 | at GLV | ||
| 9/21/2019 | Lake Erie (3-8,2-5) | 14 | at | Hillsdale | 34 | |||
| 9/28/2019 | Walsh (3-8,2-5) | 0 | at | Hillsdale | 30 | |||
| 10/5/2019 | Concord (1-10) | 14 | at | Hillsdale | 38 | MtnE | ||
| 10/12/2019 | Hillsdale | 37 | at | Northwood (1-10) | 30 | at GLIAC | ||
| 10/19/2019 | Hillsdale | 16 | at | Findlay (7-4,5-2) | 41 | |||
| 10/26/2019 | Kentucky Wesleyan (1-10,1-6) | 14 | at | Hillsdale | 41 | |||
| 11/2/2019 | Hillsdale | 56 | at | Alderson-Broaddus (1-9,1-6) | 21 | |||
| 11/9/2019 | Hillsdale | 24 | at | Tiffin (9-2,7-0) | 35 | |||
| 11/16/2019 | Ohio Dominican (7-3,6-1) | 17 | at | Hillsdale | 7 |
| vs Hillsdale | vs Other Opponents | Hillsdale compared to OOs | |
| Record: | 5-6 | 42-65 | |
| Points Scored: | 23.91 | 26.50 | 2.59 |
| Points Allowed: | 28.91 | 28.95 | -0.04 |
| Margin: | -5.00 | -2.45 | 2.55 |
| Total Points: | 52.82 | 55.45 | -2.63 |