| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 5:00 PM | Varsity | Scrimmage | Normal | Home | WCA | | | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Derby | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | |
| SAT 9/2 | 10:00 AM | Varsity | Scrimmage | Normal | Home | East Granby | | | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Shepaug Valley | Loss | 0-10 | | Shepaug Valley High School - Shepaug Valley Varsity Soccer Field | |
| WED 9/13 | 4:00 PM | Varsity | League | Normal | Away | Northwestern | Loss | 0-7 | | Northwestern Regional H.S. - Varsity Soccer Field | |
| FRI 9/15 | 3:45 PM | Varsity | League | Normal | Home | Thomaston | Loss | 1-2 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| SAT 9/16 | Forfeit | Varsity | League | Forfeit | Home | Gilbert | Win | 1-0 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| WED 9/20 | 3:45 PM | Varsity | League | Normal | Away | Terryville | Win | 1-0 | | Terryville High School - Soccer Field | |
| FRI 9/22 | 3:45 PM | Varsity | League | Normal | Home | Housatonic Regional | Loss | 0-6 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| WED 9/27 | 3:45 PM | Varsity | League | Normal | Home | Nonnewaug | Loss | 1-5 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| SUN 10/1 | 7:30 PM | Varsity | League | Normal | Away | Litchfield | Loss | 0-2 | | Plumb Hill Field Complex - Varsity Soccer Field | 12:00 PM |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Home | Northwestern | Loss | 0-4 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| THU 10/5 | Forfeit | Varsity | League | Forfeit | Away | Gilbert | Win | 1-0 | | Walker Field - Walker Field | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Shepaug Valley | Loss | 1-7 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| FRI 10/13 | 3:45 PM | Varsity | League | Normal | Away | Thomaston | Loss | 1-2 | | Thomaston Nystrom Park - Nystrom Park Field | |
| TUE 10/17 | 6:00 PM | Varsity | League | Normal | Away | Nonnewaug | Loss | 0-2 | | Nonnewaug High School - Varsity Field | |
| WED 10/18 | 3:45 PM | Varsity | League | Normal | Away | Housatonic Regional | Loss | 0-3 | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| MON 10/23 | 8:00 PM | Varsity | League | Normal | Home | Litchfield | Loss | 0-1 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |
| FRI 10/27 | 3:45 PM | Varsity | League | Normal | Home | Terryville | Loss | 0-2 | | Wamogo Regional High School - Wamogo Varsity Soccer Field | |