| 9/7/2019 | Wayne State NE (4-7,4-7) | 20 | at | Winona State | 37 | | | |
| 9/14/2019 | Winona State | 12 | at | Sioux Falls (8-4,8-3) | 34 | | | |
| 9/19/2019 | Upper Iowa (2-9,2-9) | 0 | at | Winona State | 28 | | | |
| 9/28/2019 | Winona State | 6 | at | Minnesota State-Mankato (14-1,11-0) | 20 | | | |
| 10/5/2019 | Winona State | 28 | at | Minnesota State-Moorhead (6-5,6-5) | 26 | | | |
| 10/13/2019 | Minot State (3-8,3-8) | 3 | at | Winona State | 49 | | | |
| 10/19/2019 | Winona State | 27 | at | Bemidji State (8-3,8-3) | 14 | | | |
| 10/26/2019 | Saint Cloud State (4-7,4-7) | 17 | at | Winona State | 38 | | | |
| 11/2/2019 | Winona State | 41 | at | Southwest Minnesota State (3-8,3-8) | 13 | | | |
| 11/9/2019 | Augustana SD (9-3,9-2) | 26 | at | Winona State | 25 | | | |
| 11/16/2019 | Winona State | 20 | at | Concordia-St Paul (6-5,6-5) | 10 | | | |
| 12/7/2019 | Nebraska-Kearney (7-5) | 50 | at | Winona State | 33 | | | MAIAA |