| 8/29/2019 | Rocky Mountain (4-7) | 23 | at | Dickinson State | 21 | Front | ||
| 9/7/2019 | Dickinson State | 34 | at | Jamestown (2-9) | 0 | at GPAC | ||
| 9/21/2019 | Wisconsin-La Crosse (7-3) | 17 | at | Dickinson State | 23 | WIAC (D3) | ||
| 9/28/2019 | Waldorf (7-3,5-2) | 21 | at | Dickinson State | 28 | OT | ||
| 10/5/2019 | Dickinson State | 79 | at | Mayville State (3-8,1-6) | 14 | |||
| 10/13/2019 | Dickinson State | 31 | at | Dakota State (5-5,3-4) | 14 | |||
| 10/19/2019 | Presentation (1-9,1-6) | 21 | at | Dickinson State | 42 | |||
| 10/26/2019 | Dickinson State | 22 | at | Valley City State (7-3,5-2) | 23 | |||
| 11/2/2019 | Dickinson State | 30 | at | Waldorf (7-3,5-2) | 28 | |||
| 11/9/2019 | Mayville State (3-8,1-6) | 13 | at | Dickinson State | 63 | |||
| 11/23/2019 | Dickinson State | 14 | at | Morningside (14-0) | 57 | NAIA Playoffs | at GPAC |
| vs Dickinson State | vs Other Opponents | Dickinson State compared to OOs | |
| Record: | 3-8 | 57-46 | |
| Points Scored: | 21.00 | 29.89 | 8.89 |
| Points Allowed: | 35.18 | 27.41 | 7.77 |
| Margin: | -14.18 | 2.48 | 16.66 |
| Total Points: | 56.18 | 57.30 | -1.12 |