| Woodland Varsity Boys Soccer |
| Greens Farms Academy (Scrim.) (V) Mon. 8/29, 3:45 - Away - Greens Farms Academy-Greens Farms Academy - Turf Blue |
| Watertown (V) T 1-1 Sat. 9/10, 10:00 - Away - Watertown High-John J Mills Complex @ Watertown HS |
| Wolcott (V) W 3-0 Tue. 9/13, 6:00 - Away - Wolcott High School-Monroe Field |
| Ansonia (V) W 4-0 Fri. 9/16, 3:45 - Home - Woodland High School-Woodland Soccer Field |
| Pomperaug (V) L 4-1 Sat. 9/17, 12:00 - Away - Pomperaug High School-Stadium |
| Holy Cross (V) T 1-1 Fri. 9/23, 3:45 - Home - Woodland High School-Woodland Soccer Field |
| Torrington (V) T 1-1 Tue. 9/27, 6:30 - Away - Torrington High School-Robert Frost Sports Complex |
| Derby (V) W 9-1 Thu. 9/29, 6:00 - Away - Leo F. Ryan Athletic Complex-DeFilippo Field |
| Naugatuck (V) W 1-0 Mon. 10/3, 3:45 - Home - Woodland High School-Woodland Soccer Field |
| Kennedy (V) Thu. 10/6, 3:45 - Home - Woodland High School-Woodland Soccer Field Driving Directions*Game Rosters |
| Wilby (V) Tue. 10/11, 3:30 - Away - Wilby High School-Pedro DeBrito Field Driving Directions*Game Rosters |
| Portland (V) Thu. 10/13, 4:00 - Home - Woodland High School-Woodland Soccer Field Driving Directions*Game Rosters |
| Crosby (V) Fri. 10/14, 3:45 - Home - Woodland High School-Woodland Soccer Field Driving Directions*Game Rosters |
| WCA (V) Tue. 10/18, 6:30 - Away - Municipal Stadium Complex-Ray Snyder, Sr. Turf Field Driving Directions*Game Rosters |
| Oxford (V) Thu. 10/20, 3:00 - Home - Woodland High School-Woodland Soccer Field Driving Directions*Game Rosters |
| Seymour (V) Mon. 10/24, 6:00 - Away - Seymour High School-Seymour High School Turf Field Driving Directions*Game Rosters |
| St. Paul Catholic (V) Wed. 10/26, 5:30 - Home - Woodland High School-Woodland Football Field Driving Directions*Game Rosters |
| CIAC Tournament Playdowns (V) Sat. 11/5, 2:00 - Away - Higher Seed |
| CIAC Tournament First Round (V) Mon. 11/7, 2:00 - Away - Higher Seed |
| CIAC Tournament Second Round (V) Wed. 11/9, 2:00 - Away - Higher Seed |
| CIAC Tournament Quarterfinals (V) Fri. 11/11, 2:00 - Away - Higher Seed |
| CIAC Tournament Semifinals (V) Tue. 11/15, TBA - Away - Neutral Site |
| CIAC Tournament Semifinals (V) Wed. 11/16, TBA - Away - Neutral Site |
| CIAC Tournament Semifinals (V) Thu. 11/17, TBA - Away - Neutral Site |
| CIAC Tournament Finals (V) Sat. 11/19, TBA - Away - Dillon Stadium |
| CIAC Tournament Finals (V) Sun. 11/20, TBA - Away - Dillon Stadium |