| 9/1/2018 | Chicago | 17 | at | Washington U (8-2) | 24 | at CCIW | ||
| 9/8/2018 | Simpson (7-3) | 21 | at | Chicago | 0 | IIAC | ||
| 9/22/2018 | Illinois College (4-6,4-4) | 9 | at | Chicago | 56 | |||
| 9/29/2018 | Chicago | 49 | at | Cornell IA (5-5,4-4) | 0 | |||
| 10/6/2018 | Chicago | 49 | at | Lawrence (2-8,2-7) | 0 | |||
| 10/13/2018 | St Norbert (10-2,8-0) | 21 | at | Chicago | 20 | |||
| 10/20/2018 | Chicago | 63 | at | Beloit (1-9,1-8) | 0 | |||
| 10/27/2018 | Ripon (7-3,6-2) | 6 | at | Chicago | 35 | |||
| 11/3/2018 | Chicago | 28 | at | Macalester (5-5,3-5) | 21 | |||
| 11/10/2018 | Lake Forest (6-4,5-3) | 16 | at | Chicago | 48 |
| vs Chicago | vs Other Opponents | Chicago compared to OOs | |
| Record: | 3-7 | 52-40 | |
| Points Scored: | 11.80 | 28.04 | 16.24 |
| Points Allowed: | 36.50 | 25.73 | 10.77 |
| Margin: | -24.70 | 2.31 | 27.01 |
| Total Points: | 48.30 | 53.77 | -5.47 |