| Date | Week | Home | Score | Away | Score | |
| 8/19/2021 | 1 | Milwaukee Reagan (NC) | 24 | Milwaukee Bay View/Milw Lifelong Learning | 8 | |
| 8/27/2021 | 2 | Milwaukee Marshall/Carmen NW/Milw Juneau/Milw Languages | 19 | Milwaukee Bay View/Milw Lifelong Learning | 7 | |
| 9/2/2021 | 3 | Milwaukee Bay View/Milw Lifelong Learning | 20 | Milwaukee Hamilton/Audubon Tech | 62 | |
| 9/10/2021 | 4 | *Milwaukee Reagan (NC) | 20 | Milwaukee Bay View/Milw Lifelong Learning | 14 | |
| 9/16/2021 | 5 | Milwaukee Bay View/Milw Lifelong Learning | 0 | Milwaukee Riverside/Golda Meir | 1 | |
| 9/24/2021 | 6 | Milwaukee Bradley Tech/Milw Arts | 34 | Milwaukee Bay View/Milw Lifelong Learning | 20 | |
| 10/8/2021 | 8 | Milwaukee Bay View/Milw Lifelong Learning | 0 | Milwaukee King | 55 | |
| 10/14/2021 | 9 | Milwaukee Bay View/Milw Lifelong Learning | 1 | Milwaukee Madison | 0 | |