| 9/2/2021 | Concordia-St Paul (1-10,1-10) | 6 | at | Winona State | 47 | | | |
| 9/11/2021 | Winona State | 27 | at | Minnesota State-Moorhead (5-6,5-6) | 13 | | | |
| 9/18/2021 | Minnesota-Duluth (9-3,9-2) | 29 | at | Winona State | 23 | | | |
| 9/25/2021 | Winona State | 48 | at | Mary (4-7,4-7) | 38 | | | |
| 10/2/2021 | Winona State | 21 | at | Wayne State NE (7-4,7-4) | 38 | | | |
| 10/9/2021 | Northern State (7-4,7-4) | 52 | at | Winona State | 49 | | | |
| 10/16/2021 | Southwest Minnesota State (2-9,2-9) | 14 | at | Winona State | 26 | | | |
| 10/23/2021 | Winona State | 14 | at | Sioux Falls (8-3,8-3) | 10 | | | |
| 10/30/2021 | Winona State | 20 | at | Augustana SD (9-3,9-3) | 38 | | | |
| 11/6/2021 | Upper Iowa (1-10,1-10) | 12 | at | Winona State | 40 | | | |
| 11/13/2021 | Minnesota State-Mankato (6-5,6-5) | 16 | at | Winona State | 18 | | | |