Estadio: Dorman Gymnasium Round: 1
| NCAAB | 2018/12/30 22:00 | Upper Iowa v Winona State Warriors | W | 82-76 |
| NCAAB | 2018/12/01 22:00 | Winona State Warriors v Upper Iowa | L | 72-50 |
| NCAAB | 2019/11/23 19:00 | Upper Iowa v Missouri Southern State | L | 73-98 |
| NCAAB | 2019/11/17 20:00 | Central Oklahoma v Upper Iowa | W | 70-83 |
| NCAAB | 2019/11/17 01:00 | Central Missouri v Upper Iowa | L | 70-65 |
| NCAAB | 2019/11/10 00:45 | Lincoln (MO) v Upper Iowa | L | 61-59 |
| NCAAB | 2019/11/08 22:30 | Pittsburg State v Upper Iowa | W | 62-73 |
| NCAAB | 2019/02/23 23:30 | Upper Iowa v Concordia St Paul | W | 95-77 |
| NCAAB | 2019/02/23 01:30 | Upper Iowa v Minnesota State-Mankato Mavericks | L | 75-77 |
| NCAAB | 2019/02/17 00:00 | Sioux Falls Cougars v Upper Iowa | L | 80-60 |
| NCAAB | 2019/11/17 19:00 | Winona State Warriors v Michigan Tech | W | 62-59 |
| NCAAB | 2019/11/14 01:00 | Winona State Warriors v Clarke | L | 70-73 |
| NCAAB | 2019/11/09 20:15 | Washburn v Winona State Warriors | L | 67-54 |
| NCAAB | 2019/11/08 20:15 | Missouri Southern State v Winona State Warriors | L | 71-50 |
| NCAAB | 2019/02/23 23:30 | Winona State Warriors v Minnesota State-Mankato Mavericks | W | 84-56 |
| NCAAB | 2019/02/23 01:30 | Winona State Warriors v Concordia St Paul | L | 71-75 |
| NCAAB | 2019/02/17 00:00 | Southwest Minnesota State v Winona State Warriors | L | 69-67 |
| NCAAB | 2019/02/16 01:30 | Sioux Falls Cougars v Winona State Warriors | L | 84-80 |