| Winona St. Games/Schedule |
| Nov. 8, 2019 | Round 4 (Regular Season) | Winona St. - Missouri So. | 50-71  |
| Nov. 9, 2019 | Round 5 (Regular Season) | Washburn - Winona St. | 67-54 |
| Nov. 13, 2019 | Round 9 (Regular Season) | Clarke - Winona St. | 73-70 |
| Nov. 17, 2019 | Round 13 (Regular Season) | Michigan Tech - Winona St. | 59-62  |
| Nov. 23, 2019 | Round 19 (Regular Season) | Bethany Lutheran - Winona St. | 83-96 |
| Nov. 26, 2019 | Round 22 (Regular Season) | Viterbo - Winona St. | 66-75 |
| Nov. 30, 2019 | Round 25 (Regular Season) | Winona St. - Upper Iowa | 79-84 |
| Dec. 6, 2019 | Round 31 (Regular Season) | Winona St. - Augustana, SD | 78-91 |
| Dec. 7, 2019 | Round 32 (Regular Season) | Winona St. - Wayne St., NE | 63-70 |
| Dec. 14, 2019 | Round 39 (Regular Season) | Concordia-St.Paul - Winona St. | 77-79 |
| Dec. 21, 2019 | Round 46 (Regular Season) | Upper Iowa - Winona St. | 80-85 |
| Jan. 3, 2020 | Round 53 (Regular Season) | Winona St. - MSU Moorhead | 89-77 |
| Jan. 4, 2020 | Round 54 (Regular Season) | Winona St. - Northern St. | 68-72 |
| Jan. 10, 2020 | Round 60 (Regular Season) | Wayne St., NE - Winona St. | 102-97 |
| Jan. 11, 2020 | Round 61 (Regular Season) | Augustana, SD - Winona St. | 65-79 |
| Jan. 17, 2020 | Round 66 (Regular Season) | Minn.-Crookston - Winona St. | 66-80 |
| Jan. 18, 2020 | Round 67 (Regular Season) | Bemidji St. - Winona St. | 74-82 |
| Jan. 24, 2020 | Round 73 (Regular Season) | Winona St. - SW Minnesota St. | 63-55 |
| Jan. 25, 2020 | Round 74 (Regular Season) | Winona St. - Sioux Falls | 85-87 |
| Jan. 31, 2020 | Round 80 (Regular Season) | Minn.-Duluth - Winona St. | 57-85 |
| Feb. 1, 2020 | Round 81 (Regular Season) | St.Cloud St. - Winona St. | 90-83 |
| Feb. 7, 2020 | Round 87 (Regular Season) | Winona St. - Minot St. | 73-68 |
| Feb. 8, 2020 | Round 88 (Regular Season) | Winona St. - Mary | 86-83 |
| Feb. 14, 2020 | Round 94 (Regular Season) | Sioux Falls - Winona St. | 51-49 |
| Feb. 21, 2020 | Round 101 (Regular Season) | Winona St. - Concordia-St.Paul | 74-60 |
| Feb. 22, 2020 | Round 102 (Regular Season) | Winona St. - Minn.St.-Mankato | 79-72 |
| Feb. 26, 2020 | Round 106 (Regular Season) | Minn.-Crookston - Winona St. | 57-88 |
| Feb. 29, 2020 | Round 109 (Regular Season) | Winona St. - Minn.-Duluth | 72-76 |
