| 9/7/2019 | Washington U (7-3) | 43 | at | Chicago | 7 | CCIW | ||
| 9/14/2019 | Chicago | 23 | at | Simpson (5-5) | 27 | at ARC | ||
| 9/28/2019 | Lake Forest (7-3,6-3) | 10 | at | Chicago | 27 | |||
| 10/5/2019 | Chicago | 48 | at | Beloit (1-9,1-7) | 0 | |||
| 10/12/2019 | Knox (3-6,2-5) | 6 | at | Chicago | 37 | |||
| 10/19/2019 | Chicago | 56 | at | Cornell IA (4-5,3-4) | 7 | |||
| 11/2/2019 | Monmouth IL (7-3,7-0) | 21 | at | Chicago | 20 | OT | ||
| 11/9/2019 | Chicago | 20 | at | Illinois College (6-3,5-2) | 14 | |||
| 11/16/2019 | Lake Forest (7-3,6-3) | 21 | at | Chicago | 35 |
| vs Chicago | vs Other Opponents | Chicago compared to OOs | |
| Record: | 3-6 | 44-32 | |
| Points Scored: | 16.56 | 24.74 | 8.18 |
| Points Allowed: | 30.33 | 22.76 | 7.57 |
| Margin: | -13.77 | 1.98 | 15.75 |
| Total Points: | 46.89 | 47.50 | -0.61 |