| Date | Week | Home | Score | Away | Score | |
| 8/26/2023 | 2 | Milwaukee South | 16 | Milwaukee Vincent/Destiny | 14 | |
| 9/1/2023 | 3 | Milwaukee Vincent/Destiny | 14 | Obama SCTE | 10 | |
| 9/7/2023 | 4 | Milwaukee Madison | 16 | Milwaukee Vincent/Destiny | 42 | |
| 9/15/2023 | 5 | Milwaukee Vincent/Destiny | 6 | Milwaukee Washington/Fuller Collegiate | 26 | |
| 9/21/2023 | 6 | Milwaukee Pulaski/Carmen South/Carmen SE | 30 | Milwaukee Vincent/Destiny | 0 | |
| 9/28/2023 | 7 | Milwaukee Vincent/Destiny | 0 | Milwaukee North | 18 | |
| 10/5/2023 | 8 | Milwaukee Reagan (NC) | 54 | Milwaukee Vincent/Destiny | 28 | |
| 10/12/2023 | 9 | Milwaukee Vincent/Destiny | 0 | Milwaukee Bradley Tech/Milw Arts | 14 | |