Milwaukee Madison
Milwaukee City (Blackbourn)
| Date | Week | Home | Score | Away | Score | |
| 9/9/2021 | 4 | Milwaukee Vincent/Destiny | 36 | Milwaukee Madison | 8 | |
| 9/16/2021 | 5 | Milwaukee Madison | 1 | Milwaukee South | 0 | |
| 9/16/2021 | 5 | Milwaukee Bradley Tech/Milw Arts (NC) | 37 | *Milwaukee Madison | 14 | |
| 9/23/2021 | 6 | Milwaukee Washington/Fuller Collegiate (NC) | 12 | *Milwaukee Madison | 6 | |
| 9/23/2021 | 6 | Milwaukee Madison | 1 | Obama SCTE | 0 | |
| 10/8/2021 | 8 | Milwaukee Pulaski/Carmen South/Carmen SE | 14 | Milwaukee Madison | 22 | |
| 10/14/2021 | 9 | Milwaukee Bay View/Milw Lifelong Learning | 1 | Milwaukee Madison | 0 | |
* Denotes the game does not count towards playoff calculation for the team (exhibition only)