| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/1 | 3:30 PM | Junior Varsity | Scrimmage | Normal | Away | Bethel | | | | New Fairfield High School - Marty Morgan Field | 2:25 PM |
| Brookfield | | |
| Newtown | | |
| New Fairfield | | |
| New Milford | | |
| Ridgefield | | |
| Weston | | |
| SAT 9/9 | Canceled | Junior Varsity | League | Canceled | Home | Watertown | | | | Shepaug Valley High School - Joan Gauthey Field | |
| FRI 9/15 | 4:00 PM | Junior Varsity | Non-League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Stadium Field | 2:45 PM |
| SAT 9/16 | 9:00 PM | Junior Varsity | Scrimmage | Normal | Away | Litchfield | | | | Nonnewaug High School - Turf Field | 7:45 AM |
| Nonnewaug | | |
| Wamogo | | |
| Northwestern | | |
| Thomaston | | |
| FRI 9/22 | 5:00 PM | Junior Varsity | League | Normal | Home | Northwestern | | | | Shepaug Valley High School - Joan Gauthey Field | |
| TUE 10/3 | 5:00 PM | Junior Varsity | League | Normal | Away | Thomaston | Tied | 0-0 | | Thomaston High School - Field Hockey Field | 2:00 PM |
| THU 10/5 | 5:00 PM | Junior Varsity | League | Normal | Home | Nonnewaug | | | | Shepaug Valley High School - Joan Gauthey Field | |
| SAT 10/7 | 10:00 AM | Junior Varsity | Non-League | Normal | Away | Weston | | | | Weston High School - WHS Lower Turf Field | 8:00 AM |
| WED 10/11 | 5:00 PM | Junior Varsity | League | Normal | Away | Wamogo | | | | Wamogo High School - Field Hockey Field | 2:25 PM |
| THU 10/12 | 5:00 PM | Junior Varsity | League | Normal | Home | Lewis Mills | | | | Shepaug Valley High School - Joan Gauthey Field | |
| FRI 10/13 | Canceled | Junior Varsity | League | Canceled | Away | Watertown | | | | Watertown High - John J Mills Complex @ Watertown HS | 4:00 PM |
| MON 10/16 | 5:00 PM | Junior Varsity | League | Normal | Home | Thomaston | Tied | 1-1 | | Shepaug Valley High School - Joan Gauthey Field | |
| WED 10/18 | 5:00 PM | Junior Varsity | League | Normal | Away | Northwestern | | | | Northwestern Regional H.S. - Field Hockey Field | 2:00 PM |
| THU 10/19 | 4:15 PM | Junior Varsity | League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - JV Field | 1:30 PM |
| SAT 10/21 | Canceled | Junior Varsity | Scrimmage | Canceled | Away | Northwestern | | | | Nonnewaug High School - Turf Field | 7:45 AM |
| Nonnewaug | | |
| Litchfield | | |
| Wamogo | | |
| Thomaston | | |
| SUN 10/22 | 2:30 PM | Junior Varsity | League | Normal | Away | Litchfield | | | | Plumb Hill Field Complex - Field Hockey Field | 11:40 AM |
| MON 10/23 | 5:00 PM | Junior Varsity | Non-League | Normal | Away | Danbury | | | | Danbury High School - Grass Field Hockey Field | 4:00 PM |
| WED 10/25 | 5:15 PM | Junior Varsity | League | Normal | Home | Litchfield | | | | Shepaug Valley High School - Joan Gauthey Field | |
| SAT 10/28 | 1:00 PM | Junior Varsity | League | Normal | Away | | | | | The Frederick Gunn School - Turf Field | |