| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Branford | | | | Daniel Hand High School - Turf Field | 7:00 AM - 1 Bus |
| Conard | | |
| Daniel Hand | | |
| Guilford | | |
| Sacred Heart Academy | | |
| Simsbury | | |
| TUE 9/3 | 5:00 PM | Varsity | League | Normal | Home | Lauralton Hall | Win | 6-2 | | Stonington High School - Palmer Field (Turf Stadium) | |
| THU 9/5 | 4:15 PM | Varsity | League | Normal | Away | Woodstock Academy | Win | 6-0 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | 2:15 PM - 1 Bus - FH Only |
| SAT 9/7 | 1:30 PM | Varsity | League | Normal | Away | Guilford | Loss | 1-2 | | Guilford High School - Kavanaugh Turf Field and Track | 10:15 AM - 1 Bus |
| THU 9/12 | 7:30 PM | Varsity | League | Normal | Away | Fitch | Win | 3-0 | | Groton Middle School - Groton Middle School-Turf Feld | 5:00 PM - 1 Bus |
| TUE 9/17 | 5:00 PM | Varsity | League | Normal | Home | Waterford | Win | 8-1 | | Stonington High School - Palmer Field (Turf Stadium) | |
| THU 9/19 | 5:00 PM | Varsity | League | Normal | Home | Killingly | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| MON 9/23 | 6:30 PM | Varsity | League | Normal | Home | NFA | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| THU 9/26 | 6:30 PM | Varsity | League | Normal | Away | East Lyme | | | | East Lyme High School - Dick North Turf Field | 3:45 PM - 1 Bus |
| TUE 10/1 | 5:00 PM | Varsity | League | Normal | Home | Woodstock Academy | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| MON 10/7 | 5:00 PM | Varsity | League | Normal | Home | Fitch | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| THU 10/10 | 3:45 PM | Varsity | League | Normal | Away | Killingly | | | | Killingly High School - Morgan Field | 1:45 PM - 1 Bus - w/ jv |
| SAT 10/12 | 1:00 PM | Varsity | Non-League | Normal | Home | North Branford | | | | Stonington High School - Palmer Field (Turf Stadium) | |
| TUE 10/15 | 3:45 PM | Varsity | League | Normal | Away | Waterford | | | | Waterford High School - Alumni Turf Field/Track | 2:00 PM - 1 Bus - w/ JV |
| THU 10/17 | 4:00 PM | Varsity | League | Normal | Away | NFA | | | | Norwich Free Academy - Turf Field | 2:30 PM - 1 Bus |
| SAT 10/19 | 2:00 PM | Varsity | Non-League | Normal | Away | Avon | | | | Avon High School - Turf Field | 11:15 AM - 1 Bus - w/ JV |
| TUE 10/22 | 5:00 PM | Varsity | League | Normal | Home | East Lyme | | | | Stonington High School - Palmer Field (Turf Stadium) | |