| Date | Time | Type | Home School | Away School | Site |
| MON 4/7 | 3:45 PM | League | Killingly Intermediate | Brooklyn MS | Killingly Intermediate School - KIS Softball Field |
| TUE 4/8 | 3:45 PM | League | North Haven MS | Amity MS - Orange | North Haven Middle School - North Haven Middle School Softball Field |
| MON 4/21 | 3:30 PM | League | Killingly Intermediate | Plainfield Central School | Killingly Intermediate School - KIS 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 4/22 | 4:00 PM | League | Nathan Hale Ray MS | Lyme-Old Lyme MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| THU 4/24 | 3:45 PM | League | Haddam-Killingworth MS | Nathan Hale Ray MS | Haddam Killingworth Middle School - Field 1 |
| FRI 4/25 | Canceled | League | Polson MS | | Polson MS - Green Hill Softball Field - Grass |
| MON 4/28 | 3:30 PM | League | Killingly Intermediate | Woodstock MS | Killingly Intermediate School - KIS Softball Field |
| MON 4/28 | 3:45 PM | League | John Winthrop Middle School | Haddam-Killingworth MS | John Winthrop Middle School - JWMS SB |
| TUE 4/29 | 3:45 PM | League | North Haven MS | New Haven MS | North Haven Middle School - North Haven Middle School Softball Field |
| WED 4/30 | 3:45 PM | League | Haddam-Killingworth MS | Eliot MS | Haddam Killingworth Middle School - Field 1 |
| WED 4/30 | 4:00 PM | League | John Winthrop Middle School | Strong MS | John Winthrop Middle School - JWMS SB |
| WED 4/30 | 4:00 PM | League | Nathan Hale Ray MS | Old Saybrook MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| FRI 5/2 | 3:45 PM | League | Haddam-Killingworth MS | Westbrook MS | Haddam Killingworth Middle School - Field 1 |
| FRI 5/2 | 4:00 PM | League | Nathan Hale Ray MS | Portland MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| MON 5/5 | 3:45 PM | League | Killingly Intermediate | Brooklyn MS | Killingly Intermediate School - KIS Softball Field |
| TUE 5/6 | 4:00 PM | League | John Winthrop Middle School | Nathan Hale Ray MS | John Winthrop Middle School - JWMS SB |
| WED 5/7 | 3:30 PM | League | Killingly Intermediate | Plainfield Central School | Killingly Intermediate School - KIS Softball Field |
| THU 5/8 | 3:45 PM | League | Haddam-Killingworth MS | Lyme-Old Lyme MS | Haddam Killingworth Middle School - Field 1 |
| THU 5/8 | 4:00 PM | League | John Winthrop Middle School | Portland MS | John Winthrop Middle School - JWMS SB |
| THU 5/8 | 4:00 PM | League | Nathan Hale Ray MS | Eliot MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| WED 5/14 | 3:45 PM | League | John Winthrop Middle School | Westbrook MS | John Winthrop Middle School - JWMS SB |
| THU 5/15 | 3:45 PM | League | North Haven MS | Shelton Intermediate | North Haven Middle School - North Haven Middle School Softball Field |
| FRI 5/16 | 3:45 PM | League | Haddam-Killingworth MS | Old Saybrook MS | Haddam Killingworth Middle School - Field 1 |
| FRI 5/16 | 4:00 PM | League | John Winthrop Middle School | North Branford Intermediate | John Winthrop Middle School - JWMS SB |
| TUE 5/20 | 3:45 PM | League | North Haven MS | Adams MS | North Haven Middle School - North Haven Middle School Softball Field |
| TUE 5/20 | 4:00 PM | League | Nathan Hale Ray MS | Haddam-Killingworth MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| THU 5/22 | 3:45 PM | League | Haddam-Killingworth MS | John Winthrop Middle School | Haddam Killingworth Middle School - Field 1 |
| THU 5/22 | 4:00 PM | League | Nathan Hale Ray MS | Strong MS | Nathan Hale-Ray MS - NHRMS Softball Field |
| FRI 5/23 | 3:45 PM | League | North Haven MS | Bailey MS | North Haven Middle School - North Haven Middle School Softball Field |