| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 6:30 p.m. | Varsity | League | Normal | Away | WaterburyCareer | Loss | 1-2 | | Municipal Stadium-Ray Snyder, Sr. Turf Field | |
| SAT 10/3 | 9:00 a.m. | Varsity | League | Normal | Away | Crosby | Loss | 0-7 | | Kennedy HS-CHS - Jimmy Lee Stadium (Turf) | |
| TUE 10/6 | 6:30 p.m. | Varsity | League | Normal | Away | Wilby | Win | 2-0 | | Municipal Stadium-Ray Snyder, Sr. Turf Field | |
| TUE 10/13 | 3:30 p.m. | Varsity | League | Normal | Home | WFKaynorRVT | Tied | 3-3 | | J F Kennedy High School Turf-Kennedy Turf field | |
| THU 10/15 | 6:00 p.m. | Varsity | League | Normal | Home | WaterburyCareer | Loss | 1-6 | | Municipal Stadium (Waterbury, CT)-Municipal Stadium | |
| TUE 10/20 | 3:30 p.m. | Varsity | League | Normal | Home | Crosby | Loss | 0-5 | | J F Kennedy High School Turf-Kennedy Turf field | |
| FRI 10/23 | 3:30 p.m. | Varsity | League | Normal | Home | Wilby | Loss | 1-2 | | Municipal Stadium (Waterbury, CT)-Municipal Stadium | |
| SAT 10/24 | 2:30 p.m. | Varsity | League | Normal | Away | SacredHeart | Loss | 1-4 | | Municipal Stadium-Ray Snyder, Sr. Turf Field | |
| MON 10/26 | 3:30 p.m. | Varsity | League | Normal | Home | SacredHeart | Loss | 0-1 | | J F Kennedy High School Turf-Kennedy Turf field | |
| FRI 10/30 | 3:30 p.m. | Varsity | League | Normal | Home | Wilby | Loss | 0-1 | | J F Kennedy High School Turf-Kennedy Turf field | |
| MON 11/2 | 3:00 p.m. | Varsity | League | Normal | Home | SacredHeart | Loss | 0-2 | | J F Kennedy High School Turf-Kennedy Turf field | |
| THU 11/5 | 3:30 p.m. | Varsity | League | Normal | Away | WFKaynorRVT | Tied | 2-2 | | Municipal Stadium-Ray Snyder, Sr. Turf Field | |