| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Niagara/Goodman/Pembine (NC) | 7 | Brillion | 39 | |
| 8/30/2019 | 2 | Brillion | 48 | Weyauwega-Fremont (NC) | 28 | |
| 9/6/2019 | 3 | Brillion | 34 | Roncalli | 0 | |
| 9/13/2019 | 4 | Sheboygan Falls | 34 | Brillion | 19 | |
| 9/20/2019 | 5 | Brillion | 59 | Valders | 6 | |
| 9/27/2019 | 6 | Brillion | 0 | Kiel | 35 | |
| 10/4/2019 | 7 | Two Rivers | 20 | Brillion | 27 | |
| 10/11/2019 | 8 | Chilton | 28 | Brillion | 6 | |
| 10/18/2019 | 9 | Brillion | 27 | New Holstein | 42 | |