| Date | Week | Home | Score | Away | Score | |
| 8/22/2019 | 1 | Milwaukee South (NC) | 12 | Milwaukee Bay View/Lifelong Learning | 42 | |
| 8/30/2019 | 2 | Milwaukee Bay View/Lifelong Learning | 0 | Milwaukee Riverside/Golda Meir | 57 | |
| 9/5/2019 | 3 | Milwaukee Pulaski/Carmen South/Carmen Southeast (NC) | 8 | Milwaukee Bay View/Lifelong Learning | 56 | |
| 9/14/2019 | 4 | Milwaukee Bay View/Lifelong Learning | 12 | Milwaukee Bradley/Milw Arts | 52 | |
| 9/19/2019 | 5 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 50 | Milwaukee Bay View/Lifelong Learning | 0 | |
| 9/26/2019 | 6 | Milwaukee Washington/Collegiate/Science | 14 | Milwaukee Bay View/Lifelong Learning | 36 | |
| 10/4/2019 | 7 | Milwaukee Bay View/Lifelong Learning | 6 | Milwaukee Hamilton/Audubon | 12 | 1OT |
| 10/10/2019 | 8 | Milwaukee King | 50 | Milwaukee Bay View/Lifelong Learning | 6 | |
| 10/17/2019 | 9 | Milwaukee Bay View/Lifelong Learning | 18 | Milwaukee Washington/Collegiate/Science (NC) | 0 | |