| Buena Vista 50, Woodland Park High School 21 | Dec. 2 | Details |
| Pagosa Springs 49, Woodland Park High School 36 | Dec. 3 | Details |
| Pueblo County 41, Woodland Park High School 29 | Dec. 6 | Details |
| Woodland Park High School 65, Denver North 16 | Dec. 8 | Details |
| Woodland Park High School 51, Dolores Huerta Preparatory 18 | Dec. 9 | Details |
| Woodland Park High School 36, Summit 16 | Dec. 10 | Details |
| Woodland Park High School 34, Pueblo Centennial 25 | Dec. 13 | Details |
| Coronado 45, Woodland Park High School 19 | Jan. 5 | Details |
| Vista Ridge 45, Woodland Park High School 36 | Jan. 7 | Details |
| Discovery Canyon 28, Woodland Park High School 26 | Jan. 10 | Details |
| Sierra 54, Woodland Park High School 32 | Jan. 13 | Details |
| Canon City 66, Woodland Park High School 36 | Jan. 14 | Details |
| Palmer Ridge 50, Woodland Park High School 19 () | Jan. 17 | Details |
| Lewis-Palmer High 33, Woodland Park High School 21 | Jan. 20 | Details |
| Cheyenne Mountain High School 56, Woodland Park High School 31 () | Jan. 24 | Details |
| Mitchell 52, Woodland Park High School 41 () | Jan. 26 | Details |
| Harrison vs. Woodland Park High School at Harrison () | Jan. 28 @ 2:30 p.m. | Map |
| Vista Ridge 32, Woodland Park High School 31 () | Jan. 31 | Details |
| Mesa Ridge High School 53, Woodland Park High School 9 () | Feb. 2 | Details |
| Air Academy High School 52, Woodland Park High School 10 () | Feb. 4 | Details |
| Sand Creek 57, Woodland Park High School 30 | Feb. 7 | Details |
| Falcon 55, Woodland Park High School 26 () | Feb. 10 | Details |
| Widefield High School 46, Woodland Park High School 23 () | Feb. 16 | Details |
