| 8/27/2009 | Carson-Newman 12 @ Winona St 17 | |
| 9/5/2009 | Winona St 52 @ Northern St SD 17 | † |
| 9/12/2009 | Winona St 19 @ Bemidji St 24 | † |
| 9/19/2009 | Winona St 45 @ Concordia-St Paul 24 | † |
| 9/26/2009 | Minn St-Mankato 34 @ Winona St 13 | † |
| 10/3/2009 | SW Minnesota St 33 @ Winona St 41 | † |
| 10/10/2009 | Winona St 46 @ Upper Iowa 9 | † |
| 10/17/2009 | Wayne St NE 48 @ Winona St 25 | † |
| 10/24/2009 | Minnesota-Crookston 7 @ Winona St 70 | † |
| 10/31/2009 | Winona St 23 @ Augustana SD 21 | † |
| 11/7/2009 | Minnesota-Duluth 41 @ Winona St 16 | † |