| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 3/22 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Darien | | | | Darien High School - DHS Softball - Varsity Field | |
| WED 3/27 | 4:15 PM | Varsity | Scrimmage | Normal | Home | Lauralton Hall | | | | Westhill High School - Varsity Softball Field | |
| SAT 3/30 | 11:00 AM | Varsity | Non-League | Normal | Away | Lyman Hall | Win | 7-3 | | Lyman Hall High School - Varsity Softball Field | |
| FRI 4/5 | 4:00 PM | Varsity | Non-League | Normal | Home | Immaculate | Win | 4-1 | | Westhill High School - Varsity Softball Field | |
| MON 4/8 | 5:00 PM | Varsity | Non-League | Normal | Away | Brien McMahon | Win | 12-1 | | Brien McMahon High School - Softball Diamond | |
| TUE 4/9 | 4:00 PM | Varsity | Non-League | Normal | Home | Joel Barlow | Win | 12-0 | | Westhill High School - Varsity Softball Field | |
| WED 4/10 | 4:30 PM | Varsity | League | Normal | Away | Greenwich | Win | 1-0 | | Greenwich High School - Softball Field | |
| MON 4/15 | 4:00 PM | Varsity | League | Normal | Away | Darien | Loss | 0-2 | | Darien High School - DHS Softball - Varsity Field | |
| TUE 4/16 | 4:30 PM | Varsity | League | Normal | Home | Trumbull | Loss | 1-9 | | Westhill High School - Varsity Softball Field | |
| WED 4/17 | 12:00 PM | Varsity | League | Normal | Home | Ridgefield | Loss | 0-4 | | Westhill High School - Varsity Softball Field | |
| FRI 4/19 | 12:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 1-4 | | Danbury High School - V Softball field | |
| MON 4/22 | 4:15 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 2-3 | | Fairfield Ludlowe High School - Sturges Park | |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 1-2 | | Fairfield Warde High School - Softball Diamond | |
| FRI 4/26 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 14-2 | | Westhill High School - Varsity Softball Field | |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 13-7 | | Westhill High School - Varsity Softball Field | |
| THU 5/2 | 6:30 PM | Varsity | League | Normal | Away | Stamford | Win | 6-2 | | Troy Complex - Diamond 1 | |
| FRI 5/3 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 6-9 | | St. Joseph High School - Softball Diamond | |
| MON 5/6 | 6:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 2-4 | | Waveny Park - Orchard Field | |
| WED 5/8 | 4:30 PM | Varsity | League | Normal | Home | Wilton | Win | 6-2 | | Westhill High School - Varsity Softball Field | |
| MON 5/13 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Win | 4-3 | | Westhill High School - Varsity Softball Field | |
| TUE 5/14 | 4:00 PM | Varsity | League | Normal | Home | Staples | Win | 8-4 | | Westhill High School - Varsity Softball Field | |
| SAT 5/18 | 10:00 AM | Varsity | League | Normal | Away | Bridgeport Central | Win | 15-0 | | Bridgeport Central - Varsity Softball Field | |
| TUE 5/21 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Darien | | | | Darien High School - DHS Softball - Varsity Field | |
| WED 5/22 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Staples | | | | Staples High School - Wakeman Softball Field | |