| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Baldwin-Woodville | 12 | Edgar (NC) | 26 | |
| 8/29/2019 | 2 | Gale-Ettrick-Trempealeau (NC) | 24 | Baldwin-Woodville | 30 | 2OT |
| 9/6/2019 | 3 | Amery | 0 | Baldwin-Woodville | 51 | |
| 9/13/2019 | 4 | New Richmond | 14 | Baldwin-Woodville | 16 | |
| 9/20/2019 | 5 | Baldwin-Woodville | 35 | Osceola | 7 | |
| 9/27/2019 | 6 | St. Croix Central | 41 | Baldwin-Woodville | 14 | |
| 10/4/2019 | 7 | Baldwin-Woodville | 44 | Ellsworth | 26 | |
| 10/11/2019 | 8 | Prescott | 0 | Baldwin-Woodville | 30 | |
| 10/18/2019 | 9 | Baldwin-Woodville | 50 | Somerset | 14 | |