| Date | Week | Home | Score | Away | Score | |
| 8/25/2023 | 2 | Milwaukee Bradley Tech/Milw Arts | 0 | Milwaukee Hamilton/Audubon Tech | 6 | |
| 8/31/2023 | 3 | Milwaukee Reagan | 56 | Milwaukee Bradley Tech/Milw Arts | 38 | |
| 9/8/2023 | 4 | Milwaukee Bradley Tech/Milw Arts | 8 | Milwaukee Riverside/Golda Meir | 48 | |
| 9/14/2023 | 5 | Obama SCTE (NC) | 14 | Milwaukee Bradley Tech/Milw Arts | 34 | |
| 9/22/2023 | 6 | Milwaukee Bay View/Milw Lifelong Learning | 14 | Milwaukee Bradley Tech/Milw Arts | 20 | |
| 9/28/2023 | 7 | Milwaukee Bradley Tech/Milw Arts | 6 | Milwaukee King | 57 | |
| 10/6/2023 | 8 | Milwaukee Marshall/Carmen NW/Milw Juneau/Milw Languages | 54 | Milwaukee Bradley Tech/Milw Arts | 6 | |
| 10/12/2023 | 9 | Milwaukee Vincent/Destiny | 0 | Milwaukee Bradley Tech/Milw Arts | 14 | |