| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Jonathan Law | | | | Woodland High School - Woodland Soccer Field | |
| FRI 9/1 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Sheehan | | | | Woodland High School - Woodland Soccer Field | |
| THU 9/7 | 8:00 PM | Varsity | Non-League | Normal | Away | Pomperaug | Tied | 1-1 | | Pomperaug High School - Stadium | 5:00 PM |
| SAT 9/9 | 10:30 AM | Varsity | Non-League | Normal | Home | Hamden | Win | 6-2 | | Woodland High School - Woodland Soccer Field | |
| TUE 9/12 | 3:30 PM | Varsity | League | Normal | Away | Ansonia | Win | 3-0 | | Chargers Field on Prindle Ave - Chargers Field | 2:15 PM |
| FRI 9/15 | 3:45 PM | Varsity | League | Normal | Home | Holy Cross | Tied | 1-1 | | Woodland High School - Woodland Soccer Field | |
| TUE 9/19 | 6:00 PM | Varsity | League | Normal | Away | Torrington | Win | 5-1 | | Torrington High School - Robert Frost Sports Complex | 4:00 PM |
| FRI 9/22 | 3:45 PM | Varsity | League | Normal | Home | Wolcott | Win | 3-1 | | Woodland High School - Woodland Soccer Field | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Naugatuck | Win | 6-0 | | Naugatuck High School - Veterans Field | 2:15 PM |
| THU 9/28 | 4:45 PM | Varsity | League | Normal | Home | St. Paul/Lewis Mills | Win | 9-0 | | Woodland High School - Woodland Soccer Field | |
| MON 10/2 | 6:30 PM | Varsity | League | Normal | Away | Watertown | Win | 4-0 | | Municipal stadium - Municipal stadium | 5:00 PM |
| MON 10/9 | 10:30 AM | Varsity | League | Normal | Home | Oxford | Win | 4-0 | | Woodland High School - Woodland Soccer Field | |
| FRI 10/13 | 6:00 PM | Varsity | League | Normal | Away | Seymour | Win | 4-0 | | Seymour High School - turf field | 4:30 PM |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Away | Holy Cross | Win | 3-0 | | Municipal Stadium Complex (Waterbury, CT) - Ray Snyder, Sr. Turf Field | 5:00 PM |
| TUE 10/17 | 3:45 PM | Varsity | League | Normal | Home | Derby | Win | 9-0 | | Woodland High School - Woodland Soccer Field | |
| THU 10/19 | 6:00 PM | Varsity | League | Normal | Home | Naugatuck | Win | 9-1 | | Woodland High School - Woodland Soccer Field | |
| TUE 10/24 | 4:00 PM | Varsity | League | Normal | Away | St. Paul/Lewis Mills | Win | 3-0 | | St. Paul Catholic HS - McPhee Field | 2:15 PM |
| WED 10/25 | 3:45 PM | Varsity | League | Normal | Home | Watertown | Win | 2-1 | | Woodland High School - Woodland Soccer Field | |
| SAT 10/28 | 11:00 AM | Varsity | Postseason | Normal | Home | Seymour | Win | 5-1 | | Woodland High School - Woodland Soccer Field | |
| MON 10/30 | 5:00 PM | Varsity | Postseason | Normal | Home | Ansonia | Win | 1-0 | | Wolcott High School - Turf Field | |
| WED 11/1 | 5:00 PM | Varsity | Postseason | Normal | Home | Watertown | | | | Municipal Stadium Complex (Waterbury, CT) - Ray Snyder, Sr. Turf Field | |
| MON 11/6 | 2:00 PM | Varsity | Postseason | Normal | Home | Plainville | Win | 4-0 | | Woodland High School - Woodland Soccer Field | |
| WED 11/8 | 2:00 PM | Varsity | Postseason | Normal | Home | Plainfield | Win | 3-0 | | Woodland High School - Woodland Soccer Field | |
| FRI 11/10 | 1:00 PM | Varsity | Postseason | Normal | Home | RHAM | Win | 1-0 | | Woodland High School - Woodland Soccer Field | |
| TUE 11/14 | 7:00 PM | Varsity | Postseason | Normal | Home | Bacon Academy | Loss | 0-1 | | Veteran's Stadium-Willow Brook Park - New Britain HS | |