| Date | Week | Home | Score | Away | Score | |
| 8/23/2019 | 1 | Wittenberg-Birnamwood (NC) | 34 | Northland Pines | 0 | |
| 8/30/2019 | 2 | Northland Pines | 27 | Lakeland (NC) | 32 | |
| 9/6/2019 | 3 | Rib Lake/Prentice (NC) | 0 | Northland Pines | 62 | |
| 9/13/2019 | 4 | Northland Pines | 7 | Hurley (NC) | 12 | |
| 9/20/2019 | 5 | Crandon (NC) | 0 | Northland Pines | 28 | |
| 9/27/2019 | 6 | Coleman (NC) | 48 | Northland Pines | 7 | |
| 10/4/2019 | 7 | Northland Pines | 42 | Niagara/Goodman/Pembine (NC) | 14 | |
| 10/11/2019 | 8 | Northland Pines | 13 | Highland (NC) | 7 | |
| 10/18/2019 | 9 | Northland Pines | 38 | Crivitz (NC) | 28 | |