Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 8/24/2023 | 2 | Obama SCTE | 8 | Milwaukee North | 6 | 1OT |
| 9/1/2023 | 3 | Milwaukee Vincent/Destiny | 14 | Obama SCTE | 10 | |
| 9/7/2023 | 4 | Obama SCTE | 26 | Milwaukee South | 12 | |
| 9/14/2023 | 5 | Obama SCTE | 14 | Milwaukee Bradley Tech/Milw Arts (NC) | 34 | |
| 9/21/2023 | 6 | Milwaukee Madison | 0 | Obama SCTE | 1 | |
| 9/29/2023 | 7 | Obama SCTE | 14 | Milwaukee Washington/Fuller Collegiate | 36 | |
| 10/5/2023 | 8 | Milwaukee Pulaski/Carmen South/Carmen SE | 44 | Obama SCTE | 14 | |
| 10/12/2023 | 9 | Obama SCTE | 0 | Milwaukee Riverside/Golda Meir | 28 | |