| 9/12/2009 | Chicago 37 @ Kenyon 36 | |
| 9/19/2009 | Wabash 48 @ Chicago 10 | |
| 9/26/2009 | Elmhurst 31 @ Chicago 6 | |
| 10/10/2009 | Chicago 38 @ Oberlin 17 | |
| 10/17/2009 | Chicago 28 @ Macalester 24 | |
| 10/24/2009 | Denison 7 @ Chicago 38 | |
| 10/31/2009 | Case Western Reserve 38 @ Chicago 24 | † |
| 11/7/2009 | Chicago 37 @ Washington U 44 | † |
| 11/14/2009 | Carnegie Mellon 7 @ Chicago 24 | † |