| Date | Week | Home | Score | Away | Score | |
| 8/19/2021 | 1 | Milwaukee Reagan | 24 | Milwaukee Bay View/Milw Lifelong Learning (NC) | 8 | |
| 8/27/2021 | 2 | Brookfield Academy (NC) | 29 | Milwaukee Reagan | 6 | |
| 9/3/2021 | 3 | Milwaukee Reagan | 34 | Milwaukee Pulaski/Carmen South/Carmen SE | 20 | |
| 9/10/2021 | 4 | *Milwaukee Reagan | 20 | Milwaukee Bay View/Milw Lifelong Learning (NC) | 14 | |
| 9/10/2021 | 4 | Milwaukee Reagan | 1 | Milwaukee North | 0 | |
| 9/16/2021 | 5 | *Milwaukee King (NC) | 38 | Milwaukee Reagan | 8 | |
| 9/23/2021 | 6 | Milwaukee South | 0 | Milwaukee Reagan | 1 | |
| 9/23/2021 | 6 | *Milwaukee Reagan | 6 | Milwaukee Marshall/Carmen NW/Milw Juneau/Milw Languages (NC) | 50 | |
| 10/1/2021 | 7 | Milwaukee Hamilton/Audubon Tech (NC) | 22 | *Milwaukee Reagan | 16 | |
| 10/1/2021 | 7 | Milwaukee Reagan | 1 | Obama SCTE | 0 | |
| 10/8/2021 | 8 | Milwaukee Vincent/Destiny | 14 | Milwaukee Reagan | 34 | |
| 10/15/2021 | 9 | Milwaukee Reagan | 58 | Milwaukee Bradley Tech/Milw Arts | 27 | |