| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 9/5 | 9:00 a.m. | Varsity | League | Normal | Away | Choate | | | | Choate Rosemary Hall-BVP soccer field | |
| SAT 9/10 | 7:30 p.m. | Varsity | League | Normal | Home | Guilford | Loss | 0-1 | | Madison Surf Club-Strong Field | |
| TUE 9/13 | 6:30 p.m. | Varsity | League | Normal | Away | Xavier | Loss | 1-4 | | Xavier High School-Larry McHugh Field | |
| THU 9/15 | 6:00 p.m. | Varsity | League | Normal | Home | Shelton | Loss | 0-1 | | Madison Surf Club-Strong Field | |
| TUE 9/20 | 7:00 p.m. | Varsity | League | Normal | Away | CareerMagnet | Win | 1-0 | | Bowen Field-Football Field | |
| THU 9/22 | 7:00 p.m. | Varsity | League | Normal | Away | WilburCross | Win | 3-0 | | Bowen Field-Football Field | |
| SAT 9/24 | 2:00 p.m. | Varsity | League | Normal | Away | FairfieldCollegePreparatory | Tied | 1-1 | | Fairfield University-Rafferty Stadium | |
| TUE 9/27 | 7:00 p.m. | Varsity | League | Normal | Home | WestHaven | Win | 1-0 | | Madison Surf Club-Strong Field | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Home | JonathanLaw | Win | 3-2 | | Madison Surf Club-Strong Field | |
| MON 10/3 | 5:00 p.m. | Varsity | League | Normal | Away | Guilford | Loss | 0-1 | | Guilford High School-Kavanaugh Turf Field and Track | |
| FRI 10/7 | 7:00 p.m. | Varsity | League | Normal | Home | Xavier | Loss | 0-1 | | Madison Surf Club-Strong Field | |
| SAT 10/15 | 1:00 p.m. | Varsity | League | Normal | Home | CareerMagnet | Win | 7-0 | | Madison Surf Club-Strong Field | |
| MON 10/17 | 7:00 p.m. | Varsity | League | Normal | Home | WilburCross | Loss | 0-2 | | Madison Surf Club-Strong Field | |
| THU 10/20 | 7:00 p.m. | Varsity | League | Normal | Home | FairfieldCollegePreparatory | Loss | 0-4 | | Madison Surf Club-Strong Field | |
| SAT 10/22 | 6:00 p.m. | Varsity | League | Normal | Away | WestHaven | Win | 1-0 | | West Haven High School-Ken Strong Stadium | |
| MON 10/24 | 6:00 p.m. | Varsity | League | Normal | Away | JonathanLaw | Win | 6-0 | | Jonathan Law High School-Lawmen Stadium | |
| THU 10/27 | 7:00 p.m. | Varsity | League | Normal | Away | Shelton | Tied | 0-0 | | Shelton High School-Finn Stadium | |
| SAT 11/12 | 1:00 p.m. | Varsity | League | Normal | Away | Guilford | | | | Guilford High School-Kavanaugh Turf Field and Track | |