| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 4/6 | 4:00 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 9-2 | | WHS Varsity Softball Field | |
| FRI 4/8 | 4:00 p.m. | Varsity | League | Normal | Away | Weston | Win | 11-1 | | Hurlbutt El. School, Weston | |
| MON 4/11 | 4:00 p.m. | Varsity | League | Normal | Home | Immaculate | Win | 6-2 | | WHS Varsity Softball Field | |
| WED 4/13 | 4:30 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 12-3 | | Central H.S. Varsity Softball Field | |
| FRI 4/15 | 3:00 p.m. | Varsity | League | Normal | Home | Greenwich | Win | 7-1 | | WHS Varsity Softball Field | |
| MON 4/18 | 4:30 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 0-9 | | St. Joseph High School | |
| WED 4/20 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Win | 8-3 | | WHS Varsity Softball Field | |
| FRI 4/22 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 1-4 | | WHS Varsity Softball Field | |
| SAT 4/23 | 10:00 a.m. | Varsity | League | Normal | Away | Brookfield | Loss | 1-2 | | BHS Softball Field | |
| MON 4/25 | 4:15 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 2-11 | | RHS Upper Grass Field | |
| WED 4/27 | 6:30 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Loss | 1-4 | | WHS Varsity Softball Field | |
| FRI 4/29 | 4:30 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 3-8 | | Danbury High School Varsity Softball Field | |
| MON 5/2 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Win | 4-3(9) | | WHS Varsity Softball Field | |
| THU 5/5 | 6:30 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 1-9 | | WHS Varsity Softball Field | |
| MON 5/9 | 4:15 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Win | 24-6 | | Brien McMahon HS | |
| TUE 5/10 | 4:30 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 3-15 | | Varsity Softball Field | |
| WED 5/11 | 6:30 p.m. | Varsity | League | Normal | Home | Staples | Win | 3-1 | | WHS Varsity Softball Field | |
| THU 5/12 | 6:30 p.m. | Varsity | League | Normal | Away | NewCanaan | Win | 6-2 | | Waveny Park - Orchard Field | |
| MON 5/16 | 6:30 p.m. | Varsity | League | Normal | Home | Westhill | Loss | 3-6 | | WHS Varsity Softball Field | |
| WED 5/18 | 4:15 p.m. | Varsity | League | Normal | Away | Norwalk | Win | 6-5(8) | | Ray Barry Field, NHS | |