| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Hayward/La Courte Oreilles | 42 | Barron | 18 | |
| 8/30/2019 | 2 | Barron | 27 | Ladysmith | 44 | |
| 9/6/2019 | 3 | Cumberland | 50 | Barron | 1 | |
| 9/13/2019 | 4 | Saint Croix Falls | 63 | Barron | 14 | |
| 9/20/2019 | 5 | Barron | 7 | Northwestern | 52 | |
| 9/27/2019 | 6 | Cameron | 0 | Barron | 41 | |
| 10/4/2019 | 7 | Barron | 7 | Bloomer | 48 | |
| 10/11/2019 | 8 | Chetek-Weyerhaeuser | 28 | Barron | 6 | |
| 10/18/2019 | 9 | Barron | 21 | Spooner | 26 | |