| Date | Week | Home | Score | Away | Score | |
| 8/22/2019 | 1 | Kenosha St. Joseph Catholic Academy (NC) | 34 | Milwaukee Bradley/Milw Arts | 8 | |
| 8/30/2019 | 2 | Milwaukee Hamilton/Audubon | 0 | Milwaukee Bradley/Milw Arts | 16 | |
| 9/5/2019 | 3 | Milwaukee Bradley/Milw Arts | 0 | Milwaukee King | 50 | |
| 9/14/2019 | 4 | Milwaukee Bay View/Lifelong Learning | 12 | Milwaukee Bradley/Milw Arts | 52 | |
| 9/19/2019 | 5 | Milwaukee Bradley/Milw Arts | 22 | Milwaukee Washington/Collegiate/Science | 6 | |
| 9/27/2019 | 6 | Milwaukee South (NC) | 8 | Milwaukee Bradley/Milw Arts | 50 | |
| 10/4/2019 | 7 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 28 | Milwaukee Bradley/Milw Arts | 6 | |
| 10/12/2019 | 8 | Milwaukee Bradley/Milw Arts | 6 | Milwaukee Riverside/Golda Meir | 46 | |
| 10/17/2019 | 9 | Milwaukee Bradley/Milw Arts | 58 | Milwaukee Madison (NC) | 0 | |