| 9/2/2023 | Claremont-Mudd-Scripps (8-2) | 24 | at | Chicago | 15 | SCIAC | ||
| 9/9/2023 | Chicago | 6 | at | Monmouth IL (9-2,8-1) | 39 | |||
| 9/16/2023 | Knox (3-7,3-6) | 0 | at | Chicago | 63 | |||
| 9/30/2023 | Chicago | 48 | at | Beloit (2-8,1-8) | 7 | |||
| 10/7/2023 | Illinois College (9-2,8-1) | 41 | at | Chicago | 20 | |||
| 10/14/2023 | Ripon (5-5,5-4) | 6 | at | Chicago | 21 | |||
| 10/21/2023 | Chicago | 34 | at | Cornell IA (6-4,6-3) | 47 | |||
| 10/28/2023 | Lawrence (0-10,0-9) | 12 | at | Chicago | 55 | |||
| 11/4/2023 | Chicago | 48 | at | Grinnell (2-8,2-7) | 14 | |||
| 11/11/2023 | Chicago | 15 | at | Lake Forest (7-3,6-3) | 14 |
| vs Chicago | vs Other Opponents | Chicago compared to OOs | |
| Record: | 4-6 | 47-45 | |
| Points Scored: | 20.40 | 26.85 | 6.45 |
| Points Allowed: | 32.50 | 27.11 | 5.39 |
| Margin: | -12.10 | -0.26 | 11.84 |
| Total Points: | 52.90 | 53.96 | -1.06 |