| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Chetek-Weyerhaeuser | 40 | Cameron | 0 | |
| 8/30/2019 | 2 | Bloomer | 50 | Chetek-Weyerhaeuser | 14 | |
| 9/6/2019 | 3 | Chetek-Weyerhaeuser | 14 | Saint Croix Falls | 55 | |
| 9/13/2019 | 4 | Chetek-Weyerhaeuser | 13 | Spooner | 49 | |
| 9/20/2019 | 5 | Hayward/La Courte Oreilles | 49 | Chetek-Weyerhaeuser | 31 | |
| 9/27/2019 | 6 | Chetek-Weyerhaeuser | 28 | Ladysmith | 26 | |
| 10/4/2019 | 7 | Cumberland | 46 | Chetek-Weyerhaeuser | 12 | |
| 10/11/2019 | 8 | Chetek-Weyerhaeuser | 28 | Barron | 6 | |
| 10/18/2019 | 9 | Northwestern | 56 | Chetek-Weyerhaeuser | 7 | |