| Woodland Varsity Football |
| Platt, Lyman Hall, SMSA Coop (Scrim.) (V) Sat. 8/27, 9:00 - Away - Falcon Field Meriden-falcon field Driving Directions |
| Pomperaug (Scrim.) (V) Thu. 9/1, 7:00 - Away - Pomperaug High School-Stadium Driving Directions |
| Oxford (V) W 38-6 Fri. 9/9, 6:00 - Away - Oxford High School-OHS Wolverine Field (Turf) |
| Ansonia (V) L 7-42 Fri. 9/16, 7:00 - Away - Nolan Field-Ansonia-Football Field |
| Watertown (V) W 47-0 Fri. 9/23, 7:00 - Away - Watertown High-John J Mills Complex @ Watertown HS |
| Derby (V) W 57-0 Fri. 9/30, 6:00 - Home - Woodland High School-Woodland Football Field |
| Torrington (V) Thu. 10/6, 7:00 - Away - Torrington High School-Robert Frost Sports Complex Driving Directions*Game Rosters |
| Wolcott (V) Fri. 10/21, 6:00 - Home - Woodland High School-Woodland Football Field Driving Directions*Game Rosters |
| St. Paul Catholic (V) Fri. 10/28, 6:00 - Home - Woodland High School-Woodland Football Field Driving Directions*Game Rosters |
| Holy Cross (V) Fri. 11/4, 6:00 - Home - Woodland High School-Woodland Football Field Driving Directions*Game Rosters |
| Naugatuck (V) Fri. 11/11, 6:00 - Home - Woodland High School-Woodland Football Field Driving Directions*Game Rosters |
| Seymour (V) Wed. 11/23, 7:00 - Away - Seymour High School-turf field Driving Directions*Game Rosters |
| CIAC Tournament Quarterfinals (V) Tue. 11/29, TBA - Away |
| CIAC Tournament Semifinals (V) Sun. 12/4, TBA - Away - Higher Seed |
| CIAC Tournament Finals (V) Sat. 12/10, TBA - Away - Neutral Site |