Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 9/4/2026 | 3 | Obama SCTE | 0 | Dr. Howard Fuller Collegiate Academy | 1 | |
| 9/17/2026 | 5 | *Milwaukee North/Milwaukee WI Conservatory of Lifelong Learning (NC) | 22 | *Obama SCTE | 0 | |
| 9/18/2026 | 5 | Milwaukee Madison | 0 | Obama SCTE | 1 | |
| 10/3/2026 | 7 | Obama SCTE | | Milwaukee South | | |
| 10/9/2026 | 8 | Milwaukee Washington | | Obama SCTE | | |
| 10/16/2026 | 9 | Obama SCTE | | Milwaukee Vincent | | |
* Denotes the game does not count towards playoff calculation for the team (exhibition only)