| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 4:30 PM | Varsity | Scrimmage | Normal | Away | | Win | 5-0 | | Mt Everett High School - Mt. Everett V Soccer Field | 12:01 AM |
| SAT 9/9 | 10:00 AM | Varsity | League | Normal | Home | Shepaug Valley | Loss | 3-6 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| MON 9/11 | Forfeit | Varsity | League | Forfeit | Away | Gilbert | Win | 1-0 | | Walker Field - Walker Field | 2:30 PM |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Thomaston | Loss | 0-3 | | Thomaston Nystrom Park - Nystrom Park Field | 2:15 PM |
| FRI 9/15 | 3:45 PM | Varsity | League | Normal | Home | Litchfield | Tied | 1-1 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Nonnewaug | Loss | 1-2 | | Nonnewaug High School - Varsity Field | 2:15 PM |
| FRI 9/22 | 3:45 PM | Varsity | League | Normal | Away | Wamogo | Win | 6-0 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | 2:30 PM |
| MON 10/2 | 3:45 PM | Varsity | League | Normal | Home | Terryville | Win | 2-1 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| TUE 10/3 | Forfeit | Varsity | League | Forfeit | Home | Gilbert | Win | 1-0 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| THU 10/5 | 3:45 PM | Varsity | League | Normal | Away | Shepaug Valley | Loss | 2-7 | | Shepaug Valley High School - Shepaug Valley Varsity Soccer Field | 2:15 PM |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Thomaston | Loss | 1-2 | | Housatonic Valley Regional High - Boys Practice Field | |
| THU 10/12 | 3:45 PM | Varsity | League | Normal | Away | Northwestern | Loss | 0-2 | | Northwestern Regional H.S. - Varsity Soccer Field | 4:00 PM |
| FRI 10/13 | 3:45 PM | Varsity | League | Normal | Away | Litchfield | Loss | 0-4 | | Plumb Hill Field Complex - Varsity Soccer Field | 2:30 PM |
| MON 10/16 | 3:45 PM | Varsity | League | Normal | Home | Northwestern | Win | 2-1 | | Housatonic Valley Regional High - Boys Practice Field | |
| WED 10/18 | 3:45 PM | Varsity | League | Normal | Home | Wamogo | Win | 3-0 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| WED 10/25 | 6:30 PM | Varsity | League | Normal | Away | Terryville | Win | 2-1 | | Terryville High School - Soccer Field | 2:15 PM |
| FRI 10/27 | 3:45 PM | Varsity | League | Normal | Home | Nonnewaug | Loss | 0-1 | | Housatonic Valley Regional High - Boys Practice Field | |
| TUE 11/7 | 5:30 PM | Varsity | Postseason | Normal | Away | St. Paul Catholic | Loss | 1-2 | | St. Paul Catholic HS - McPhee Field | 3:45 PM |