| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 4/5 | 4:15 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 4-15 | | Trumbull High School-Varsity Softball Diamond | |
| SAT 4/9 | 2:30 p.m. | Varsity | League | Normal | Away | Greenwich | Win | 10-0 | | Bruce Park Field | |
| TUE 4/12 | 4:30 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 0-14 | | Westhill High School-Varsity Softball Field | |
| SAT 4/16 | 11:00 a.m. | Varsity | League | Normal | Away | NorwichFreeAcademy | Loss | 2-15 | | Rec Fields-DePina 1 | |
| MON 4/18 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | Win | 15-2 | | Darien High School-DHS Softball - Varsity Field | |
| THU 4/21 | 4:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Loss | 9-11 | | Westhill High School-Varsity Softball Field | |
| FRI 4/22 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 15-0 | | Bridgeport Central High School-Varsity Softball Field | |
| MON 4/25 | 4:00 p.m. | Varsity | League | Normal | Home | Staples | Loss | 0-8 | | Westhill High School-Varsity Softball Field | |
| WED 4/27 | 4:00 p.m. | Varsity | League | Normal | Home | Norwalk | Win | 8-7 | | Westhill High School-Varsity Softball Field | |
| FRI 4/29 | 4:30 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 2-5 | | Fairfield Warde HS-Softball Diamond | |
| TUE 5/3 | 4:00 p.m. | Varsity | League | Normal | Away | Brookfield | Loss | 1-6 | | Brookfield High School-BHS Softball Field | |
| THU 5/5 | 4:45 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 0-10 | | St. Joseph High School-Softball Diamond | |
| TUE 5/10 | 4:30 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 1-12 | | Westhill High School-Varsity Softball Field | |
| WED 5/11 | 7:00 p.m. | Varsity | League | Normal | Home | Greenwich | Win | 10-2 | | Troy Complex | |
| THU 5/12 | 4:30 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 0-3 | | Danbury High School-V Softball field | |
| SAT 5/14 | 6:30 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 2-14 | | Troy Complex | |
| SUN 5/15 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 2-11 | | Fairfield Ludlowe High School-Sturges Park | |
| TUE 5/17 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 2-9 | | Westhill High School-Varsity Softball Field | |
| WED 5/18 | 6:30 p.m. | Varsity | League | Normal | Away | NewCanaan | Win | 7-4 | | Waveny Park-Orchard Field | |
| WED 5/25 | 4:30 p.m. | Varsity | League | Normal | Home | Bassick | Forfeit | Forfeit | | Westhill High School-Varsity Softball Field | |