| Date | Week | Home | Score | Away | Score | |
| 8/18/2023 | 1 | Greenfield (NC) | 42 | Milwaukee Reagan | 16 | |
| 8/25/2023 | 2 | Milwaukee Riverside/Golda Meir | 36 | Milwaukee Reagan | 38 | |
| 8/31/2023 | 3 | Milwaukee Reagan | 56 | Milwaukee Bradley Tech/Milw Arts | 38 | |
| 9/7/2023 | 4 | Milwaukee Bay View/Milw Lifelong Learning | 0 | Milwaukee Reagan | 28 | |
| 9/14/2023 | 5 | Milwaukee Reagan | 0 | Milwaukee King | 45 | |
| 9/21/2023 | 6 | Milwaukee Reagan | 48 | Milwaukee Marshall/Carmen NW/Milw Juneau/Milw Languages | 52 | |
| 9/29/2023 | 7 | Milwaukee Reagan | 44 | Milwaukee Hamilton/Audubon Tech | 32 | |
| 10/5/2023 | 8 | Milwaukee Reagan | 54 | Milwaukee Vincent/Destiny (NC) | 28 | |
| 10/13/2023 | 9 | Milwaukee South | 6 | Milwaukee Reagan | 48 | |