Milwaukee Madison
Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 9/18/2026 | 5 | Milwaukee Madison | 0 | Obama SCTE | 1 | |
| 9/25/2026 | 6 | Dr. Howard Fuller Collegiate Academy | | Milwaukee Madison | | |
| 10/1/2026 | 7 | Milwaukee North/Milwaukee WI Conservatory of Lifelong Learning | | Milwaukee Madison | | |
| 10/8/2026 | 8 | Milwaukee South | | Milwaukee Madison | | |
| 10/15/2026 | 9 | Milwaukee Madison | | Milwaukee Washington | | |