| Date | Time | Type | Home School | Away School | Site |
| TUE 4/8 | 3:45 PM | League | North Haven MS | Amity MS - Orange | North Haven Middle School - North Haven Middle School Softball Field |
| FRI 4/11 | 4:00 PM | Non-League | Lakeview | New Fairfield | Lakeview Regional High School - JV Softball Field |
| TUE 4/22 | 3:45 PM | League | North Haven MS | Hamden MS | North Haven Middle School - North Haven Middle School Softball Field |
| TUE 4/29 | 3:45 PM | League | North Haven MS | New Haven MS | North Haven Middle School - North Haven Middle School Softball Field |
| THU 5/15 | 3:45 PM | League | North Haven MS | Shelton Intermediate | North Haven Middle School - North Haven Middle School Softball Field |
| TUE 5/20 | 3:45 PM | League | North Haven MS | Adams MS | North Haven Middle School - North Haven Middle School Softball Field |
| FRI 5/23 | 3:45 PM | League | North Haven MS | Bailey MS | North Haven Middle School - North Haven Middle School Softball Field |