| 9/4/2021 | Washington U (7-4) | 21 | at | Chicago | 31 | CCIW | ||
| 9/11/2021 | Illinois College (5-5,5-4) | 14 | at | Chicago | 66 | |||
| 9/18/2021 | Chicago | 66 | at | Beloit (0-10,0-9) | 0 | |||
| 10/2/2021 | Knox (3-6,3-6) | 10 | at | Chicago | 45 | |||
| 10/9/2021 | Chicago | 37 | at | Monmouth IL (8-2,8-1) | 40 | |||
| 10/16/2021 | Chicago | 47 | at | Cornell IA (4-6,4-5) | 21 | |||
| 10/23/2021 | Ripon (6-3,5-3) | 14 | at | Chicago | 38 | |||
| 10/30/2021 | Chicago | 78 | at | Grinnell (2-8,2-7) | 3 | |||
| 11/6/2021 | Lawrence (2-7,1-7) | 0 | at | Chicago | 66 | |||
| 11/13/2021 | Chicago | 6 | at | Lake Forest (10-1,9-0) | 28 |
| vs Chicago | vs Other Opponents | Chicago compared to OOs | |
| Record: | 2-8 | 45-44 | |
| Points Scored: | 15.10 | 27.43 | 12.33 |
| Points Allowed: | 48.00 | 27.61 | 20.39 |
| Margin: | -32.90 | -0.18 | 32.72 |
| Total Points: | 63.10 | 55.04 | 8.06 |