| Date | Week | Home | Score | Away | Score | |
| 8/22/2019 | 1 | Milwaukee Hamilton/Audubon | 20 | Shoreland Lutheran (NC) | 21 | |
| 8/30/2019 | 2 | Milwaukee Hamilton/Audubon | 0 | Milwaukee Bradley/Milw Arts | 16 | |
| 9/6/2019 | 3 | Milwaukee Marshall/Carmen Northwest/Juneau/Languages | 28 | Milwaukee Hamilton/Audubon | 0 | |
| 9/13/2019 | 4 | Milwaukee Madison (NC) | 8 | Milwaukee Hamilton/Audubon | 46 | |
| 9/20/2019 | 5 | Milwaukee King | 46 | Milwaukee Hamilton/Audubon | 0 | |
| 9/28/2019 | 6 | Milwaukee Hamilton/Audubon | 8 | Milwaukee Riverside/Golda Meir | 43 | |
| 10/4/2019 | 7 | Milwaukee Bay View/Lifelong Learning | 6 | Milwaukee Hamilton/Audubon | 12 | 1OT |
| 10/11/2019 | 8 | Milwaukee Hamilton/Audubon | 40 | Milwaukee Washington/Collegiate/Science | 0 | |
| 10/17/2019 | 9 | Milwaukee Hamilton/Audubon | 40 | Milwaukee Pulaski/Carmen South/Carmen Southeast (NC) | 14 | |