| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Ladysmith | 26 | Cumberland | 56 | |
| 8/30/2019 | 2 | Barron | 27 | Ladysmith | 44 | |
| 9/6/2019 | 3 | Ladysmith | 0 | Northwestern | 42 | |
| 9/13/2019 | 4 | Cameron | 12 | Ladysmith | 47 | |
| 9/20/2019 | 5 | Ladysmith | 12 | Bloomer | 42 | |
| 9/27/2019 | 6 | Chetek-Weyerhaeuser | 28 | Ladysmith | 26 | |
| 10/4/2019 | 7 | Ladysmith | 16 | Spooner | 37 | |
| 10/11/2019 | 8 | Hayward/La Courte Oreilles | 35 | Ladysmith | 7 | |
| 10/18/2019 | 9 | Ladysmith | 28 | Saint Croix Falls | 35 | |