| Date | Time | Type | Home School | Away School | Site |
| WED 9/27 | Canceled | League | | | Sherman School-Sherman - Sherman |
| FRI 3/29 | 4:00 PM | Non-League | Westerly Middle School | | Westerly Middle School |
| TUE 4/2 | 4:00 PM | League | | | Thompson Middle School - Riverside Park |
| WED 4/3 | Canceled | League | | | Windham Middle School - Softball Field |
| FRI 4/5 | 3:45 PM | League | Shepaug Valley | Gilbert | Washington Primary School - Washington Primary School Softball Field |
| MON 4/8 | 3:30 PM | League | | | Thompson Middle School - Riverside Park |
| MON 4/8 | 3:45 PM | League | Gilbert | Northwestern | Rowley Field - Gilbert (Rowley Street) Field #1 |
| MON 4/8 | 4:00 PM | League | | | Brooklyn Middle School - Prince Hill |
| MON 4/8 | 4:00 PM | League | | | Putnam Middle School - PMS Softball Field (Behind School) |
| TUE 4/9 | 3:30 PM | League | | | Pomfret Community School - school field |
| TUE 4/9 | 3:45 PM | League | | ACES at Chase | Long River Middle School - Long River Middle School |
| WED 4/10 | 3:30 PM | League | | | ASHFORD SCHOOL - Softball Field |
| WED 4/10 | 3:30 PM | League | | | Plainfield Central Middle School - PCS Softball Field |
| WED 4/10 | 3:30 PM | Scrimmage | | | Rectory School - Softball Diamond |
| WED 4/10 | 3:45 PM | League | | | Long River Middle School - Long River Middle School |
| WED 4/10 | 3:45 PM | League | | | Mansfield Middle School - Softball field |
| WED 4/10 | 3:45 PM | League | | | Sherman School-Sherman - Sherman |
| WED 4/10 | 4:00 PM | League | | | Helen Baldwin Middle School - BMS School Field |
| THU 4/11 | 3:30 PM | League | | | Thompson Middle School - Riverside Park |
| THU 4/11 | 3:30 PM | League | | | Woodstock Middle School - WMS Softball Field |
| THU 4/11 | 3:45 PM | League | Gilbert | Wamogo/Litchfield | Rowley Field - Gilbert (Rowley Street) Field #1 |
| THU 4/11 | Canceled | League | | , | Mansfield Middle School - Softball field |
| FRI 4/12 | Postponed | League | | | Parish Hill Middle School - softball field |
| FRI 4/12 | Postponed | League | | | Washington Primary School - Washington Primary School Softball Field |
| MON 4/15 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield |
| TUE 4/16 | 3:30 PM | League | Aerospace/Engineering - Windsor | Comp Sci MS | LP Wilson - Softball Diamond |
| TUE 4/16 | 3:30 PM | League | | | Middle School of Plainville - Softball Field |
| TUE 4/16 | 3:30 PM | League | | | Thomas Edison Middle School - Default Facility |
| TUE 4/16 | 3:45 PM | League | | | Memorial Field - East Haven - Memorial Field |
| TUE 4/16 | 3:45 PM | League | | | Walsh Intermediate School - WIS Softball Field (185 Damascus RD) |
| TUE 4/16 | Canceled | Scrimmage | | | Vernon Center Middle School - VCMS Fields |
| WED 4/17 | 3:30 PM | League | | | Lincoln Middle School - Lincoln ms |
| WED 4/17 | 3:45 PM | League | | | Illing MS - Softball diamond |
| WED 4/17 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| WED 4/17 | 3:45 PM | League | | | Moran MS |
| WED 4/17 | 3:45 PM | Non-League | | | Tolland Middle School - TMS Softball Field |
| WED 4/17 | 3:45 PM | Scrimmage | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| WED 4/17 | Canceled | League | | | McGee MS - Softball Field |
| THU 4/18 | Canceled | Non-League | | | Bolton Center Middle School - BCS Softball Field |
| FRI 4/19 | 3:30 PM | League | Innovation MS | International MS | Chesley Park - Softball Diamond #1 |
| FRI 4/19 | 3:30 PM | League | | | Cromwell Middle School - Cromwell High School |
| FRI 4/19 | 3:30 PM | League | | | Lincoln Middle School - Lincoln ms |
| FRI 4/19 | 3:30 PM | League | | | McGee MS - Softball Field |
| FRI 4/19 | 3:30 PM | League | | | Thomas Edison Middle School - Default Facility |
| FRI 4/19 | 3:45 PM | League | | | Beman Middle School - Pat Kidney Softball Field |
| FRI 4/19 | 3:45 PM | League | | | Ellington MS - Ellington Middle School |
| FRI 4/19 | Postponed | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| MON 4/22 | 3:30 PM | League | | | Long River Middle School - Long River Middle School |
| MON 4/22 | 3:30 PM | League | | | RHAM Middle School - Veterans Park |
| MON 4/22 | 3:45 PM | League | | | Ellington MS - Ellington Middle School |
| MON 4/22 | 3:45 PM | League | | | Stafford MS - Middle School Softball Field |
| MON 4/22 | 3:45 PM | League | | | Thomas Edison Middle School - Default Facility |
| MON 4/22 | 3:45 PM | League | | | Walsh Intermediate School - WIS Softball Field (185 Damascus RD) |
| MON 4/22 | 3:45 PM | League | | | Windham Middle School - Softball Field |
| MON 4/22 | 4:00 PM | League | | | Helen Baldwin Middle School - BMS School Field |
| MON 4/22 | 4:00 PM | League | | | Lyme-Old Lyme Middle School - HS Softball Field |
| MON 4/22 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| MON 4/22 | 4:00 PM | League | | | Wallace Middle School - Crosby Softball Field |
| MON 4/22 | 4:30 PM | League | | | Adams Middle School - Softball field |
| MON 4/22 | Forfeit | League | Innovation MS | Aerospace/Engineering - Windsor | Chesley Park - Softball Diamond #1 |
| TUE 4/23 | 3:30 PM | League | | | Cromwell Middle School - Woodside Intermediate School |
| TUE 4/23 | 3:30 PM | League | | , | Har-Bur Middle School - Har-Bur Middle School Girls Softball |
| TUE 4/23 | 3:30 PM | League | Comp Sci MS | International MS | McAuliffe Park - Field #3 |
| TUE 4/23 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| TUE 4/23 | 3:30 PM | League | | | Parish Hill Middle School - softball field |
| TUE 4/23 | 3:30 PM | League | | | Wamogo Middle School Softball Field - Wamogo Regional Middle School Girls Softball |
| TUE 4/23 | 3:45 PM | League | | | Amity MS - Orange - Softball Field |
| TUE 4/23 | 3:45 PM | League | | | Bailey Middle School - Benham Hill Field |
| TUE 4/23 | 3:45 PM | League | | | Bradley School - Bradley Field |
| TUE 4/23 | 3:45 PM | League | | | Captain Nathan Hale School - softball field |
| TUE 4/23 | 3:45 PM | League | | | Dag Hammarskjold MS - Wallingford - Dag ms |
| TUE 4/23 | 3:45 PM | League | | | East Windsor MS - Middle School Softball Field |
| TUE 4/23 | 3:45 PM | League | | | Eliot MS - Softball Field |
| TUE 4/23 | 3:45 PM | League | | | Groton Middle School - Softball field |
| TUE 4/23 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field 1 |
| TUE 4/23 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield |
| TUE 4/23 | 3:45 PM | League | | | North End Middle School - Bucks Hill Park |
| TUE 4/23 | 3:45 PM | League | | ACES at Chase | Oxford Middle School - Softball Field |
| TUE 4/23 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| TUE 4/23 | 3:45 PM | League | | , , , | Stem Academy - Softball Field |
| TUE 4/23 | 3:45 PM | League | | | Walsh Intermediate School - WIS Softball Field (185 Damascus RD) |
| TUE 4/23 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| TUE 4/23 | 3:45 PM | Non-League | | | Dodd Middle School - Upper Field |
| TUE 4/23 | 3:45 PM | Non-League | | Woodstock Middle School | Groton Middle School - GMS Softball Field |
| TUE 4/23 | 4:00 PM | League | | | Adams Middle School - Softball field |
| TUE 4/23 | 4:00 PM | League | | | Amity Middle School - Bethany - Softball Field |
| TUE 4/23 | 4:00 PM | League | | | Bethel Middle School - Johnson Field |
| TUE 4/23 | 4:00 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| TUE 4/23 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| TUE 4/23 | 4:00 PM | League | | | Vernon Center Middle School - VCMS Fields |
| TUE 4/23 | 4:15 PM | League | | | West Bristol School - Softball Field |
| WED 4/24 | 3:30 PM | League | | | East Hampton MS - EH Middle Complex |
| WED 4/24 | 3:30 PM | League | | | Killingly Intermediate School - KIS Softball Field |
| WED 4/24 | 3:30 PM | League | | | North End Field - North End Field |
| WED 4/24 | 3:30 PM | League | | | Thompson Middle School - Riverside Park |
| WED 4/24 | 3:45 PM | League | ACES at Chase | | Aces at Chase - Softball Diamond |
| WED 4/24 | 3:45 PM | League | | | Brooklyn Middle School - Prince Hill |
| WED 4/24 | 3:45 PM | League | | | Dag Hammarskjold MS - Wallingford - Dag ms |
| WED 4/24 | 3:45 PM | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| WED 4/24 | 3:45 PM | League | | | Polson MS - Green Hill Softball Field - Grass |
| WED 4/24 | 3:45 PM | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| WED 4/24 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| WED 4/24 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| WED 4/24 | 4:00 PM | League | | | Helen Baldwin Middle School - BMS School Field |
| WED 4/24 | 4:00 PM | League | | | Rocky Hill High School - Softball Diamond |
| WED 4/24 | 4:45 PM | League | | | East Hartford Middle School - Softball Field |
| WED 4/24 | Canceled | League | | | Preston Plains School - Default Facility |
| WED 4/24 | Canceled | Non-League | | | Preston Plains School - Default Facility |
| THU 4/25 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| THU 4/25 | 3:30 PM | League | | | Rocky Hill H. S. Field - Rocky Hill H. S. Field |
| THU 4/25 | 3:45 PM | League | | | Beman Middle School - Pat Kidney Softball Field |
| THU 4/25 | 3:45 PM | League | | | Captain Nathan Hale School - softball field |
| THU 4/25 | 3:45 PM | League | | | City Hill Middle School - Softball field (Breen field) |
| THU 4/25 | 3:45 PM | League | | | Hamden Middle School - Softball Field |
| THU 4/25 | 3:45 PM | League | | | Illing MS - Softball diamond |
| THU 4/25 | 3:45 PM | League | | | North Haven Middle School - North Haven Middle School Softball Field |
| THU 4/25 | 3:45 PM | League | | | Polson MS - Green Hill Softball Field - Grass |
| THU 4/25 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| THU 4/25 | 3:45 PM | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| THU 4/25 | 3:45 PM | League | | | Sherman School-Sherman - Sherman |
| THU 4/25 | 3:45 PM | League | | | Tolland Middle School - TMS Softball Field |
| THU 4/25 | 3:45 PM | League | | | Totoket Valley Park - Softball Field |
| THU 4/25 | 3:45 PM | League | | | Woodbury Middle School - Softball Field |
| THU 4/25 | 4:00 PM | League | | | Degale Field - Degale Field #1 |
| THU 4/25 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| THU 4/25 | 4:00 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| THU 4/25 | 4:00 PM | League | | | Lebanon Middle School - Lebanon MS Softball Field |
| THU 4/25 | 4:00 PM | League | | | Lisbon Central School - LCS Softball Field |
| THU 4/25 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| THU 4/25 | 4:00 PM | League | | | Nathan Hale-Ray MS - NHRMS Softball Field |
| THU 4/25 | 4:00 PM | League | | | Northeast Middle School - Softball Field |
| THU 4/25 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| THU 4/25 | 4:00 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| THU 4/25 | 4:00 PM | Non-League | | | Woodstock Middle School - WMS Softball Field |
| THU 4/25 | 4:15 PM | League | | | Greene Hills Elementary - Softball Field |
| THU 4/25 | 4:30 PM | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| FRI 4/26 | 3:30 PM | League | | | East Hampton MS - EH Middle Complex |
| FRI 4/26 | 3:30 PM | League | | | Lincoln Middle School - Lincoln ms |
| FRI 4/26 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| FRI 4/26 | 3:30 PM | League | | | Plainfield Central Middle School - PCS Softball Field |
| FRI 4/26 | 3:30 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| FRI 4/26 | 3:45 PM | League | | | Middle School of Plainville - Softball Field |
| FRI 4/26 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| FRI 4/26 | 3:45 PM | League | | , , , | Stem Academy - Softball Field |
| FRI 4/26 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| FRI 4/26 | 4:00 PM | League | | | Adams Middle School - Softball field |
| FRI 4/26 | 4:00 PM | League | | | Newtown MS - Softball Field |
| FRI 4/26 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| FRI 4/26 | 4:15 PM | League | | | Memorial Middle School - MMS Softball Field |
| FRI 4/26 | Canceled | League | | | North End Field - North End Field |
| MON 4/29 | 3:30 PM | League | | | ASHFORD SCHOOL - Softball Field |
| MON 4/29 | 3:30 PM | League | | | Long River Middle School - Long River Middle School |
| MON 4/29 | 3:30 PM | League | | | Plainfield Central Middle School - PCS Softball Field |
| MON 4/29 | 3:30 PM | League | | | Pomfret Community School - school field |
| MON 4/29 | 3:30 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| MON 4/29 | 3:30 PM | Scrimmage | | | Rectory School - Softball Diamond |
| MON 4/29 | 3:45 PM | League | | | Amity MS - Orange - Softball Field |
| MON 4/29 | 3:45 PM | League | | | Bailey Middle School - Benham Hill Field |
| MON 4/29 | 3:45 PM | League | | | Brooklyn Middle School - Prince Hill |
| MON 4/29 | 3:45 PM | League | | | Depaolo Middle School - DMS Softball Field |
| MON 4/29 | 3:45 PM | League | | | Eliot MS - Softball Field |
| MON 4/29 | 3:45 PM | League | | | Ellington MS - Ellington Middle School |
| MON 4/29 | 3:45 PM | League | | | Groton Middle School - Softball field |
| MON 4/29 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field 1 |
| MON 4/29 | 3:45 PM | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| MON 4/29 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| MON 4/29 | 3:45 PM | League | Wamogo/Litchfield | Northwestern | Wamogo Regional High School - Litchfield HS Softball Fields |
| MON 4/29 | 3:45 PM | League | | | Windham Middle School - Softball Field |
| MON 4/29 | 3:45 PM | Non-League | | | Groton Middle School - GMS Softball Field |
| MON 4/29 | 4:00 PM | League | | | Chippens Hill Middle School - Softball Diamond |
| MON 4/29 | 4:00 PM | League | | | McGee MS - Softball Field |
| MON 4/29 | 4:00 PM | League | | | Nathan Hale Ray MS - Nathan Hale Ray MS |
| MON 4/29 | 4:00 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| MON 4/29 | 4:00 PM | League | | | Old Saybrook Middle School - Old Saybrook MS Softball |
| MON 4/29 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| MON 4/29 | 4:00 PM | League | | | Vernon Center Middle School - VCMS Fields |
| MON 4/29 | 4:15 PM | League | | | Colt Park - Colt Park |
| MON 4/29 | 4:15 PM | League | | | Jockey Hollow - Wolfe Park Field 4 |
| MON 4/29 | 4:15 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| MON 4/29 | 4:30 PM | League | | | Bethel Middle School - Johnson Field |
| TUE 4/30 | 3:15 PM | League | | | Moran Middle School - Moran ms |
| TUE 4/30 | 3:30 PM | League | ACES at Chase | | Aces at Chase - Softball Diamond |
| TUE 4/30 | 3:30 PM | League | | | ASHFORD SCHOOL - Softball Field |
| TUE 4/30 | 3:30 PM | League | | | Harry S. Fisher Elementary School - Softball Field |
| TUE 4/30 | 3:30 PM | League | Aerospace/Engineering - Windsor | International MS | LP Wilson - Softball Diamond |
| TUE 4/30 | 3:30 PM | League | Comp Sci MS | Innovation MS | McAuliffe Park - Field #3 |
| TUE 4/30 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| TUE 4/30 | 3:30 PM | League | | | Parish Hill Middle School - softball field |
| TUE 4/30 | 3:30 PM | League | | | RHAM Middle School - Veterans Park |
| TUE 4/30 | 3:45 PM | League | | | Amity Middle School - Bethany - Softball Field |
| TUE 4/30 | 3:45 PM | League | | | Amity MS - Orange - Softball Field |
| TUE 4/30 | 3:45 PM | League | | | Captain Nathan Hale School - softball field |
| TUE 4/30 | 3:45 PM | League | | | City Hill Middle School - Softball field (Breen field) |
| TUE 4/30 | 3:45 PM | League | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| TUE 4/30 | 3:45 PM | League | | | North End Middle School - Huntingdon Ave. Softball Field |
| TUE 4/30 | 3:45 PM | League | | | Oxford Middle School - Softball Field |
| TUE 4/30 | 3:45 PM | League | | | Polson MS - Green Hill Softball Field - Grass |
| TUE 4/30 | 3:45 PM | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| TUE 4/30 | 3:45 PM | League | | , , , | Stem Academy - Softball Field |
| TUE 4/30 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| TUE 4/30 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| TUE 4/30 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| TUE 4/30 | 3:45 PM | League | | | Windsor Locks MS - Softball Field |
| TUE 4/30 | 4:00 PM | League | | | Adams Middle School - Softball field |
| TUE 4/30 | 4:00 PM | League | | | Ansonia High School - Softball Diamond |
| TUE 4/30 | 4:00 PM | League | | | Bethel Middle School - Johnson Field |
| TUE 4/30 | 4:00 PM | League | | | Chippens Hill Middle School - Softball Diamond |
| TUE 4/30 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| TUE 4/30 | 4:00 PM | League | | | Newtown MS - Softball Field |
| TUE 4/30 | 4:00 PM | Non-League | | | Preston Plains School - Default Facility |
| TUE 4/30 | 4:00 PM | Non-League | Westerly Middle School | | Westerly Middle School |
| TUE 4/30 | 4:30 PM | League | | | Housatonic Valley Regional High - JV Softball Diamond |
| TUE 4/30 | Canceled | League | | | Bolton Center Middle School - BCS Softball Field |
| TUE 4/30 | Postponed | League | | | Carmen Arace Middle School - field |
| WED 5/1 | 3:30 PM | League | | | Beman Middle School - Pat Kidney Softball Field |
| WED 5/1 | 3:30 PM | League | | | Cromwell Middle School - Woodside Intermediate School |
| WED 5/1 | 3:30 PM | League | | | Har-Bur Middle School - Har-Bur Middle School Girls Softball |
| WED 5/1 | 3:30 PM | League | | | McGee MS - Softball Field |
| WED 5/1 | 3:30 PM | League | | | Parish Hill Middle School - softball field |
| WED 5/1 | 3:30 PM | League | | | Putnam Middle School - PMS Softball Field (Behind School) |
| WED 5/1 | 3:45 PM | League | | | Brooklyn Middle School - Prince Hill |
| WED 5/1 | 3:45 PM | League | | | Middle School of Plainville - Softball Field |
| WED 5/1 | 3:45 PM | League | | | Rumsey Hall |
| WED 5/1 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| WED 5/1 | 4:00 PM | League | | | Newtown MS - Softball Field |
| WED 5/1 | 4:00 PM | League | | | Old Saybrook Middle School - Old Saybrook MS Softball |
| WED 5/1 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| WED 5/1 | Postponed | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| THU 5/2 | 3:30 PM | League | Comp Sci MS | Aerospace/Engineering - Windsor | McAuliffe Park - Field #3 |
| THU 5/2 | 3:40 PM | League | | | East Hartford MS - Softball Field |
| THU 5/2 | 3:45 PM | League | ACES at Chase | | Aces at Chase - Softball Diamond |
| THU 5/2 | 3:45 PM | League | | | Bailey Middle School - Benham Hill Field |
| THU 5/2 | 3:45 PM | League | | | Carmen Arace Middle School - field |
| THU 5/2 | 3:45 PM | League | | | Hall Memorial School - Default Facility |
| THU 5/2 | 3:45 PM | League | | | Hamden Middle School - Softball Field |
| THU 5/2 | 3:45 PM | League | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| THU 5/2 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| THU 5/2 | 3:45 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| THU 5/2 | 3:45 PM | League | | | Oxford Middle School - Softball Field |
| THU 5/2 | 3:45 PM | League | | | Veterans Memorial Park - Vets #1 |
| THU 5/2 | 3:45 PM | League | | | Wamogo Middle School Softball Field - Wamogo Regional Middle School Girls Softball |
| THU 5/2 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| THU 5/2 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| THU 5/2 | 3:45 PM | League | | | Windsor Locks MS - Softball Field |
| THU 5/2 | 4:00 PM | League | | | ASHFORD SCHOOL - Softball Field |
| THU 5/2 | 4:00 PM | League | | | Degale Field - Degale Field #1 |
| THU 5/2 | 4:00 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| THU 5/2 | 4:00 PM | League | | , | Lebanon Middle School - Lebanon MS Softball Field |
| THU 5/2 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| THU 5/2 | 4:00 PM | League | | | Northeast Middle School - Softball Field |
| THU 5/2 | 4:00 PM | League | | | Preston Plains School - Default Facility |
| THU 5/2 | 4:00 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| THU 5/2 | 4:15 PM | League | | | Hyland Park - Hyland Park, 355 New Britain Ave. |
| THU 5/2 | 4:15 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| THU 5/2 | Canceled | League | | | Bolton Center Middle School - BCS Softball Field |
| THU 5/2 | Canceled | League | | | Tyrrell Middle School - Tyrrell Middle School |
| THU 5/2 | Postponed | League | | | North End Middle School - Bucks Hill Park |
| FRI 5/3 | 3:15 PM | League | | | North End Field - North End Field |
| FRI 5/3 | 3:30 PM | League | | | Harry S. Fisher Elementary School - Softball Field |
| FRI 5/3 | 3:30 PM | League | | | Killingly Intermediate School - KIS Softball Field |
| FRI 5/3 | 3:30 PM | League | | | Rocky Hill H. S. Field - Rocky Hill H. S. Field |
| FRI 5/3 | 3:30 PM | League | | | Thomaston Center School - Sanford Field |
| FRI 5/3 | 3:45 PM | League | | | Dag MS |
| FRI 5/3 | 3:45 PM | League | | | Dodd Middle School - Upper Field |
| FRI 5/3 | 3:45 PM | League | | | Middle School of Plainville - Softball Field |
| FRI 5/3 | 3:45 PM | League | | | North End Middle School - Huntingdon Ave. Softball Field |
| FRI 5/3 | 3:45 PM | League | | | Oxford Middle School - Softball Field |
| FRI 5/3 | 3:45 PM | League | | | Totoket Valley Park - Softball Field |
| FRI 5/3 | 3:45 PM | League | | ACES at Chase | West Side Middle School-Waterbury - Town Plot Park |
| FRI 5/3 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| FRI 5/3 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| FRI 5/3 | 4:00 PM | League | | | Moran Middle School - Moran ms |
| FRI 5/3 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| FRI 5/3 | 4:00 PM | League | | | Stafford MS - Middle School Softball Field |
| FRI 5/3 | 4:15 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| FRI 5/3 | 4:30 PM | League | | | Indian Mountain School - softball field |
| FRI 5/3 | Canceled | League | | | Bradley School - Bradley Field |
| FRI 5/3 | Canceled | League | | | Preston Plains School - Default Facility |
| MON 5/6 | 3:30 PM | League | | | Killingly Intermediate School - KIS Softball Field |
| MON 5/6 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| MON 5/6 | 3:30 PM | League | | | Rectory School - Softball Diamond |
| MON 5/6 | 3:30 PM | League | | | Windsor Locks MS - Softball Field |
| MON 5/6 | 3:45 PM | League | | | Depaolo Middle School - DMS Softball Field |
| MON 5/6 | 3:45 PM | League | | | Dodd Middle School - Upper Field |
| MON 5/6 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| MON 5/6 | 3:45 PM | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| MON 5/6 | 4:00 PM | League | | | Helen Baldwin Middle School - BMS School Field |
| MON 5/6 | 4:00 PM | League | | | Newtown MS - Softball Field |
| MON 5/6 | Canceled | League | | | RHAM Middle School - Veterans Park |
| MON 5/6 | Canceled | League | | | Wallace Middle School - Rotella Magnet School Field |
| MON 5/6 | Postponed | League | | | Haddam Killingworth Middle School - Field 1 |
| MON 5/6 | Postponed | League | | | North End Middle School - Huntingdon Ave. Softball Field |
| MON 5/6 | Rainout | League | | | Veterans Memorial Park - Veterans Park |
| TUE 5/7 | 3:30 PM | League | International MS | Comp Sci MS | Academy of International Studies - Softball Diamond |
| TUE 5/7 | 3:30 PM | League | | | Ansonia MS - softball field |
| TUE 5/7 | 3:30 PM | League | | | Harry S. Fisher Elementary School - Softball Field |
| TUE 5/7 | 3:30 PM | League | | | Lincoln Middle School - Lincoln ms |
| TUE 5/7 | 3:30 PM | League | | | Lisbon Central School - LCS Softball Field |
| TUE 5/7 | 3:30 PM | League | Aerospace/Engineering - Windsor | Innovation MS | LP Wilson - Softball Diamond |
| TUE 5/7 | 3:30 PM | League | | | Putnam Middle School - PMS Softball Field (Behind School) |
| TUE 5/7 | 3:30 PM | League | | | Rocky Hill H. S. Field - Rocky Hill H. S. Field |
| TUE 5/7 | 3:45 PM | League | | | East Windsor MS - Middle School Softball Field |
| TUE 5/7 | 3:45 PM | League | | , | Horace Porter School - Columbia Rec Park Hennequin Rd |
| TUE 5/7 | 3:45 PM | League | | | Middle School of Plainville - Softball Field |
| TUE 5/7 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| TUE 5/7 | 3:45 PM | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| TUE 5/7 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| TUE 5/7 | 3:45 PM | League | | | Veterans Memorial Park - Vets #1 |
| TUE 5/7 | 3:45 PM | League | | | Wallace Middle School - Rotella Magnet School Field |
| TUE 5/7 | 3:45 PM | League | | | Walsh Intermediate School - WIS Softball Field (185 Damascus RD) |
| TUE 5/7 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| TUE 5/7 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| TUE 5/7 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| TUE 5/7 | 3:45 PM | League | | | Winsted Rowley Field - Winsted Rowley Field |
| TUE 5/7 | 4:00 PM | League | | | Adams Middle School - Softball field |
| TUE 5/7 | 4:00 PM | League | | | Bethel Middle School - Kisling Field |
| TUE 5/7 | 4:00 PM | League | | | Captain Nathan Hale School - softball field |
| TUE 5/7 | 4:00 PM | League | | | Chippens Hill Middle School - Softball Diamond |
| TUE 5/7 | 4:00 PM | League | | | Colt Park - Colt Park |
| TUE 5/7 | 4:00 PM | League | | | Degale Field - Degale Field #1 |
| TUE 5/7 | 4:00 PM | League | | | Nathan Hale Ray MS - Nathan Hale Ray MS |
| TUE 5/7 | 4:00 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| TUE 5/7 | 4:00 PM | League | | | Old Saybrook Middle School - Old Saybrook MS Softball |
| TUE 5/7 | 4:00 PM | League | | | Rose Hill - rose hill |
| TUE 5/7 | 4:00 PM | League | | | Windham Middle School - Softball Field |
| TUE 5/7 | 4:15 PM | League | | | Memorial Middle School - MMS Softball Field |
| TUE 5/7 | Postponed | League | | | Polson MS - Green Hill Softball Field - Grass |
| WED 5/8 | 3:30 PM | League | | | East Hampton MS - EH Middle Complex |
| WED 5/8 | 4:00 PM | League | | | Tolland Middle School - TMS Softball Field |
| WED 5/8 | Canceled | Scrimmage | | | Brooklyn Middle School - Prince Hill |
| WED 5/8 | Postponed | League | | | Beman Middle School - Pat Kidney Softball Field |
| WED 5/8 | Postponed | League | | | Lyme-Old Lyme Middle School - HS Softball Field |
| THU 5/9 | 3:30 PM | League | International MS | Innovation MS | Academy of International Studies - Softball Diamond |
| THU 5/9 | 3:30 PM | League | ACES at Chase | | Aces at Chase - Softball Diamond |
| THU 5/9 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| THU 5/9 | 3:30 PM | League | | | Pomfret Community School - school field |
| THU 5/9 | 3:30 PM | League | | | Wamogo Middle School Softball Field - Plumb Hill Playing Fields |
| THU 5/9 | 3:30 PM | Non-League | | | Woodstock Middle School - WMS Softball Field |
| THU 5/9 | 3:45 PM | League | | | Amity Middle School - Bethany - Softball Field |
| THU 5/9 | 3:45 PM | League | | | Amity MS - Orange - Softball Field |
| THU 5/9 | 3:45 PM | League | | | Bailey Middle School - Benham Hill Field |
| THU 5/9 | 3:45 PM | League | | | Dodd Middle School - Upper Field |
| THU 5/9 | 3:45 PM | League | | | East Hartford Middle School - Softball Field |
| THU 5/9 | 3:45 PM | League | | | Ellington MS - Ellington Middle School |
| THU 5/9 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield |
| THU 5/9 | 3:45 PM | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| THU 5/9 | 3:45 PM | League | | | Sherman School-Sherman - Sherman |
| THU 5/9 | 3:45 PM | League | | , , , | Stem Academy - Softball Field |
| THU 5/9 | 3:45 PM | League | | | Timothy Edwards Middle School - Timothy Edwards Middle School |
| THU 5/9 | 3:45 PM | League | | | Tyrrell Middle School - Softball Field |
| THU 5/9 | 4:00 PM | League | | | Adams Middle School - Softball field |
| THU 5/9 | 4:00 PM | League | | | Lebanon Middle School - Lebanon MS Softball Field |
| THU 5/9 | 4:00 PM | League | | | Northeast Middle School - Softball Field |
| THU 5/9 | 4:00 PM | League | | | Old Saybrook Middle School - Old Saybrook MS Softball |
| THU 5/9 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| THU 5/9 | 4:00 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| THU 5/9 | 4:00 PM | League | | | Totoket Valley Park - Softball Field |
| THU 5/9 | 4:00 PM | League | | | Vernon Center Middle School - VCMS Fields |
| THU 5/9 | 4:15 PM | League | | | West Bristol School - Softball Field |
| THU 5/9 | Canceled | League | | | Captain Nathan Hale School - softball field |
| THU 5/9 | Canceled | League | | | Hamden Middle School - Softball Field |
| THU 5/9 | Canceled | League | | | Harry S. Fisher Elementary School - Softball Field |
| THU 5/9 | Canceled | League | | | Long River Middle School - Long River Middle School |
| THU 5/9 | Postponed | League | | | Wallace Middle School - Rotella Magnet School Field |
| FRI 5/10 | 3:30 PM | League | | | RHAM Middle School - Veterans Park |
| FRI 5/10 | 3:45 PM | League | | , | Captain Nathan Hale School - softball field |
| FRI 5/10 | 3:45 PM | League | | | Carmen Arace Middle School - field |
| FRI 5/10 | 3:45 PM | League | | | Moran Middle School - Moran ms |
| FRI 5/10 | 3:45 PM | League | | | Tyrrell Middle School - Softball Field |
| FRI 5/10 | 4:00 PM | League | | | Preston Plains School - Default Facility |
| FRI 5/10 | 4:15 PM | League | | | Colt Park - Colt Park |
| FRI 5/10 | Canceled | League | | | Depaolo Middle School - DMS Softball Field |
| FRI 5/10 | Canceled | Non-League | | | Preston Plains School - Default Facility |
| FRI 5/10 | Postponed | League | | | Plainfield Central Middle School - PCS Softball Field |
| FRI 5/10 | Postponed | League | | | Wallace Middle School - Rotella Magnet School Field |
| MON 5/13 | 3:30 PM | League | International MS | Aerospace/Engineering - Windsor | Academy of International Studies - Softball Diamond |
| MON 5/13 | 3:30 PM | League | | | Harry S. Fisher Elementary School - Softball Field |
| MON 5/13 | 3:30 PM | League | | | Plainfield Central Middle School - PCS Softball Field |
| MON 5/13 | 3:30 PM | League | | | Woodstock Middle School - WMS Softball Field |
| MON 5/13 | 3:30 PM | Scrimmage | | | Rectory School - Softball Diamond |
| MON 5/13 | 3:45 PM | League | | | Amity Middle School - Bethany - Softball Field |
| MON 5/13 | 3:45 PM | League | | | Depaolo Middle School - DMS Softball Field |
| MON 5/13 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field 1 |
| MON 5/13 | 3:45 PM | League | | | Illing MS - Softball diamond |
| MON 5/13 | 3:45 PM | League | | | Moran Middle School - Moran ms |
| MON 5/13 | 3:45 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| MON 5/13 | 4:00 PM | League | | | Bailey Middle School - Benham Hill Field |
| MON 5/13 | 4:00 PM | League | | ACES at Chase | Bradley School - Bradley Field |
| MON 5/13 | 4:00 PM | League | | | East Hampton MS - EH Middle Complex |
| MON 5/13 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| MON 5/13 | 4:00 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| MON 5/13 | 4:00 PM | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| MON 5/13 | 4:00 PM | League | | | Nathan Hale-Ray MS - NHRMS Softball Field |
| MON 5/13 | 4:00 PM | League | | | Preston Plains School - Default Facility |
| MON 5/13 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| MON 5/13 | 4:00 PM | League | | | Totoket Valley Park - Softball Field |
| MON 5/13 | 4:15 PM | League | | | West Bristol School - Softball Field |
| MON 5/13 | 4:30 PM | League | | Westerly Middle School | Groton Middle School - Softball field |
| MON 5/13 | 4:30 PM | League | | | Housatonic Valley Regional High - JV Softball Diamond |
| MON 5/13 | Canceled | League | | | East Windsor MS - Middle School Softball Field |
| MON 5/13 | Canceled | League | | | Preston Plains School - Default Facility |
| MON 5/13 | Postponed | League | | | Ellington MS - Softball Diamond |
| TUE 5/14 | 3:15 PM | League | | | Thomas Edison Middle School - Default Facility |
| TUE 5/14 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| TUE 5/14 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| TUE 5/14 | 3:30 PM | League | | | North End Field - North End Field |
| TUE 5/14 | 3:30 PM | League | | | Pomfret Community School - school field |
| TUE 5/14 | 3:30 PM | Non-League | | | Rose Hill - rose hill |
| TUE 5/14 | 3:45 PM | League | | | City Hill Middle School - Softball field (Breen field) |
| TUE 5/14 | 3:45 PM | League | | | East Hartford Middle School - Softball Field |
| TUE 5/14 | 3:45 PM | League | | | Hall Memorial School - Default Facility |
| TUE 5/14 | 3:45 PM | League | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| TUE 5/14 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| TUE 5/14 | 3:45 PM | League | | | North End Middle School - Bucks Hill Park |
| TUE 5/14 | 3:45 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| TUE 5/14 | 3:45 PM | League | | | Polson MS - Green Hill Softball Field - Grass |
| TUE 5/14 | 3:45 PM | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| TUE 5/14 | 3:45 PM | League | | | Wallace Middle School - Crosby Softball Field |
| TUE 5/14 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| TUE 5/14 | 3:45 PM | League | | | Windsor Locks MS - Softball Field |
| TUE 5/14 | 3:45 PM | League | | | Woodbury Middle School - Softball Field |
| TUE 5/14 | 4:00 PM | League | | | Adams Middle School - Softball field |
| TUE 5/14 | 4:00 PM | League | | | Dag Hammarskjold MS - Wallingford - Dag ms |
| TUE 5/14 | 4:00 PM | League | | | Degale Field - Degale Field #1 |
| TUE 5/14 | 4:00 PM | League | | | Lisbon Central School - Default Facility |
| TUE 5/14 | 4:00 PM | League | | | Mansfield Middle School - Softball field |
| TUE 5/14 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| TUE 5/14 | 4:00 PM | League | | | Nathan Hale Ray MS - Nathan Hale Ray MS |
| TUE 5/14 | 4:00 PM | League | | | Northeast Middle School - Softball Field |
| TUE 5/14 | 4:15 PM | League | | | Memorial Middle School - MMS Softball Field |
| TUE 5/14 | Canceled | League | | | Tyrrell Middle School - Softball Field |
| WED 5/15 | 3:30 PM | League | | | ASHFORD SCHOOL - Softball Field |
| WED 5/15 | 3:30 PM | League | | | East Hampton MS - EH Middle Complex |
| WED 5/15 | 3:30 PM | League | | | Woodstock Middle School - WMS Softball Field |
| WED 5/15 | 3:30 PM | Scrimmage | | | Killingly Intermediate School - KIS Softball Field |
| WED 5/15 | 3:45 PM | League | | | Beman Middle School - Pat Kidney Softball Field |
| WED 5/15 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field 1 |
| WED 5/15 | 3:45 PM | League | | | Kennedy Middle School-Plantsville - KMS Softball Field |
| WED 5/15 | 3:45 PM | League | | | Putnam Middle School - PMS Softball Field (Behind School) |
| WED 5/15 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| WED 5/15 | 4:00 PM | League | | | Carmen Arace Middle School - field |
| WED 5/15 | 4:00 PM | League | | Chariho Regional Middle School | Groton Middle School - Softball field |
| WED 5/15 | 4:00 PM | League | | | Suffield Middle School - MS Field |
| WED 5/15 | 4:00 PM | Non-League | | Chariho Regional Middle School | Groton Middle School - GMS Softball Field |
| WED 5/15 | 4:30 PM | League | | | Housatonic Valley Regional High - JV Softball Diamond |
| WED 5/15 | 4:30 PM | Non-League | | | North Haven Athletic Complex - Brook Field-Softball |
| WED 5/15 | Canceled | League | | | Depaolo Middle School - DMS Softball Field |
| WED 5/15 | Canceled | League | | | Eliot MS - Softball Field |
| WED 5/15 | Canceled | League | | | Ellington MS - Softball Diamond |
| WED 5/15 | Canceled | League | | | Memorial Middle School - MMS Softball Field |
| THU 5/16 | 3:30 PM | League | | | North End Field - North End Field |
| THU 5/16 | 3:45 PM | League | | | Bethel Middle School - Johnson Field |
| THU 5/16 | 3:45 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| THU 5/16 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| THU 5/16 | 3:45 PM | League | | | Tolland Middle School - TMS Softball Field |
| THU 5/16 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| THU 5/16 | 3:45 PM | League | | | Windham Middle School - Softball Field |
| THU 5/16 | Canceled | League | | | Amity MS - Orange - Softball Field |
| THU 5/16 | Canceled | League | | | Eliot MS - Softball Field |
| THU 5/16 | Canceled | League | | | North End Middle School - Bucks Hill Park |
| THU 5/16 | Canceled | League | | | Rocky Hill H. S. Field - Rocky Hill H. S. Field |
| THU 5/16 | Canceled | League | | ACES at Chase | Tyrrell Middle School - Softball Field |
| THU 5/16 | Postponed | League | | | Hyland Park - Hyland Park |
| THU 5/16 | Postponed | League | | | Parish Hill Middle School - softball field |
| THU 5/16 | Postponed | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| THU 5/16 | Rainout | League | | | East Hartford Middle School - Softball Field |
| FRI 5/17 | 3:30 PM | League | | | Parish Hill Middle School - softball field |
| FRI 5/17 | 3:30 PM | League | | | Pomfret Community School - school field |
| FRI 5/17 | 3:30 PM | League | | | RHAM High School - Softball Diamond |
| FRI 5/17 | 3:30 PM | League | | | Woodbury Middle School - Softball Field |
| FRI 5/17 | 3:45 PM | League | | | Captain Nathan Hale School - softball field |
| FRI 5/17 | 3:45 PM | League | | | Dag Hammarskjold MS - Wallingford - Dag ms |
| FRI 5/17 | 3:45 PM | League | | | Dodd Middle School - Upper Field |
| FRI 5/17 | 3:45 PM | League | | | Housatonic Valley Regional High - JV Softball Diamond |
| FRI 5/17 | 3:45 PM | League | | | Long River Middle School - Long River Middle School |
| FRI 5/17 | 3:45 PM | League | | | Moran Middle School - Moran ms |
| FRI 5/17 | 3:45 PM | League | | | Nathan Hale Ray MS - Nathan Hale-Ray High School |
| FRI 5/17 | 3:45 PM | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| FRI 5/17 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| FRI 5/17 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| FRI 5/17 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| FRI 5/17 | 4:00 PM | League | | | Newtown MS - Softball Field |
| FRI 5/17 | 4:00 PM | League | | | Stafford MS - Middle School Softball Field |
| FRI 5/17 | 4:00 PM | League | | | Totoket Valley Park - Softball Field |
| FRI 5/17 | 4:15 PM | League | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| FRI 5/17 | Canceled | League | | | North End Middle School - Huntingdon Ave. Softball Field |
| FRI 5/17 | Rainout | League | | | Bradley School - Bradley Field |
| MON 5/20 | 3:00 PM | League | | | Lisbon Central School - LCS Softball Field |
| MON 5/20 | 3:15 PM | League | | | North End Field - North End Field |
| MON 5/20 | 3:30 PM | League | ACES at Chase | | Aces at Chase - Softball Diamond |
| MON 5/20 | 3:30 PM | League | | | Ansonia MS - Ansonia ms |
| MON 5/20 | 3:30 PM | League | | , | Har-Bur Middle School - Har-Bur Middle School Girls Softball |
| MON 5/20 | 3:30 PM | League | | | Killingly Intermediate School - KIS Softball Field |
| MON 5/20 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| MON 5/20 | 3:30 PM | League | Comp Sci MS | International MS | McAuliffe Park - Field #3 |
| MON 5/20 | 3:30 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| MON 5/20 | 3:30 PM | League | | | Stafford MS - Middle School Softball Field |
| MON 5/20 | 3:30 PM | League | | | Thompson Middle School - Riverside Park |
| MON 5/20 | 3:45 PM | League | | | Illing MS - Softball diamond |
| MON 5/20 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| MON 5/20 | 3:45 PM | League | | | Sage Park Middle School - Sage Park Grass Field 1 |
| MON 5/20 | 3:45 PM | League | | , , , | Stem Academy - Softball Field |
| MON 5/20 | 3:45 PM | League | | | Veterans Memorial Park - Vets #1 |
| MON 5/20 | 3:45 PM | League | | | Winsted Rowley Field - Winsted Rowley Field |
| MON 5/20 | 4:00 PM | League | | | Hyland Park - Hyland Park, 355 New Britain Ave. |
| MON 5/20 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| MON 5/20 | 4:00 PM | League | | | Old Saybrook Middle School - Old Saybrook MS Softball |
| MON 5/20 | 4:00 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| MON 5/20 | 4:00 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| MON 5/20 | 4:00 PM | League | | | Vernon Center Middle School - VCMS Fields |
| MON 5/20 | 4:15 PM | League | | | Greene Hills Elementary - Softball Field |
| MON 5/20 | 4:15 PM | League | | | Jockey Hollow - Wolfe Park Field 4 |
| MON 5/20 | 4:15 PM | League | | | Memorial Middle School - MMS Softball Field |
| MON 5/20 | 4:15 PM | League | | | West Bristol School - Softball Field |
| MON 5/20 | 4:30 PM | League | | | Housatonic Valley Regional High - JV Softball Diamond |
| MON 5/20 | 5:00 PM | Non-League | | | Nathan Hale-Ray Middle School - Hale-Ray High School Softball Field |
| MON 5/20 | 6:00 PM | Non-League | | | Beman Middle School - Pat Kidney Softball Field |
| TUE 5/21 | 3:30 PM | League | Innovation MS | Aerospace/Engineering - Windsor | Chesley Park - Softball Diamond #1 |
| TUE 5/21 | 3:30 PM | League | | , | Har-Bur Middle School - Har-Bur Middle School Girls Softball |
| TUE 5/21 | 3:30 PM | League | | | Harry S. Fisher Elementary School - Softball Field |
| TUE 5/21 | 3:30 PM | League | | | McGee MS - Softball Field |
| TUE 5/21 | 3:30 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| TUE 5/21 | 3:30 PM | League | | | Winsted Rowley Field - Winsted Rowley Field |
| TUE 5/21 | 3:30 PM | League | | | Woodstock Middle School - WMS Softball Field |
| TUE 5/21 | 3:45 PM | League | | | City Hill Middle School - Softball field (Breen field) |
| TUE 5/21 | 3:45 PM | League | | | Dodd Middle School - Upper Field |
| TUE 5/21 | 3:45 PM | League | | | Haddam Killingworth Middle School - Field 1 |
| TUE 5/21 | 3:45 PM | League | | | Hamden Middle School - Softball Field |
| TUE 5/21 | 3:45 PM | League | | | Indian Mountain School - softball field |
| TUE 5/21 | 3:45 PM | League | | | John F. Kennedy Middle School-Enfield - Baseball Diamond |
| TUE 5/21 | 3:45 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| TUE 5/21 | 3:45 PM | League | | | Suffield Middle School - MS Field |
| TUE 5/21 | 3:45 PM | League | | | Veterans Memorial Park - Veterans Park |
| TUE 5/21 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| TUE 5/21 | 4:00 PM | League | | | Adams Middle School - Softball field |
| TUE 5/21 | 4:00 PM | League | | | Degale Field - Degale Field #1 |
| TUE 5/21 | 4:00 PM | League | | , | Horace Porter School - Rec Park Hennequin Rd |
| TUE 5/21 | 4:00 PM | League | | | Northeast Middle School - Softball Field |
| TUE 5/21 | 4:00 PM | League | | | Windsor Locks MS - Softball Field |
| TUE 5/21 | 4:15 PM | League | | | Jockey Hollow - Wolfe Park Field 4 |
| TUE 5/21 | 4:30 PM | League | | | Lyme-Old Lyme Middle School - HS Softball Field |
| TUE 5/21 | 4:30 PM | Postseason | | | Captain Nathan Hale School - softball field |
| TUE 5/21 | Canceled | League | | | Ansonia MS - Ansonia ms |
| TUE 5/21 | Canceled | League | | | Lisbon Central School - LCS Softball Field |
| TUE 5/21 | Canceled | League | | ACES at Chase | North End Middle School - Bucks Hill Park |
| TUE 5/21 | Canceled | League | | | West Side Middle School-Waterbury - Town Plot Park |
| TUE 5/21 | Postponed | League | | | Eliot MS - Softball Field |
| TUE 5/21 | Postponed | League | | | Lincoln Middle School - Lincoln ms |
| WED 5/22 | 3:00 PM | League | | | Woodstock Middle School - WMS Softball Field |
| WED 5/22 | 3:30 PM | League | | | East Hampton MS - EH Middle Complex |
| WED 5/22 | 3:30 PM | League | | | Parish Hill Middle School - softball field |
| WED 5/22 | 3:30 PM | League | | | Stafford MS - Middle School Softball Field |
| WED 5/22 | 3:45 PM | League | | | East Hartford Middle School - Softball Field |
| WED 5/22 | 3:45 PM | League | | | Illing MS - Softball diamond |
| WED 5/22 | 3:45 PM | League | | | Seymour Middle School - SMS Softball Field |
| WED 5/22 | 3:45 PM | League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| WED 5/22 | 3:45 PM | League | | | Tyrrell Middle School - Tyrrell Middle School |
| WED 5/22 | 3:45 PM | League | | | Walsh Intermediate School - WIS Softball Field (185 Damascus RD) |
| WED 5/22 | 4:00 PM | League | | | Frank Ward Strong Middle School - Strong Middle School Field |
| WED 5/22 | 4:00 PM | League | | | John Winthrop Middle School - John Winthrop Middle School |
| WED 5/22 | 4:00 PM | League | | | Lisbon Central School - LCS Softball Field |
| WED 5/22 | 4:00 PM | League | | | Lyme-Old Lyme Middle School - HS Softball Field |
| WED 5/22 | 4:00 PM | League | | | Memorial Field - East Haven - Memorial Field |
| WED 5/22 | 4:15 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| WED 5/22 | 4:30 PM | League | | | Hyland Park - Hyland Park, 355 New Britain Ave. |
| WED 5/22 | 6:00 PM | League | | | Wallace Middle School - Municipal Stadium |
| WED 5/22 | 7:00 PM | League | | | East Hartford Middle School - Softball Field |
| WED 5/22 | Canceled | League | | | Lisbon Central School - LCS Softball Field |
| WED 5/22 | Canceled | League | | | Memorial Middle School - MMS Softball Field |
| THU 5/23 | 3:30 PM | League | Innovation MS | Comp Sci MS | Chesley Park - Softball Diamond #1 |
| THU 5/23 | 3:30 PM | League | | | McGee MS - Softball Field |
| THU 5/23 | 4:00 PM | League | | | Hall Memorial School - Default Facility |
| THU 5/23 | 4:00 PM | League | | | Horace Porter School - Columbia Rec Park Hennequin Rd |
| THU 5/23 | 4:00 PM | League | | | Oxford Middle School - Softball Field |
| THU 5/23 | 4:00 PM | League | | | Totoket Valley Park - Softball Field |
| THU 5/23 | Canceled | League | | | Carmen Arace Middle School - field |
| THU 5/23 | Canceled | League | | | North End Middle School - Bucks Hill Park |
| THU 5/23 | Canceled | League | | | North Haven Athletic Complex - Brook Field-Softball |
| THU 5/23 | Canceled | League | | | Suffield Middle School - MS Field |
| THU 5/23 | Canceled | League | | | Winsted Rowley Field - Winsted Rowley Field |
| THU 5/23 | Postponed | League | | | Amity Middle School - Bethany - Softball Field |
| THU 5/23 | Postponed | League | | | Amity MS - Orange - Softball Field |
| THU 5/23 | Postponed | League | | | Woodbury Middle School - Softball Field |
| FRI 5/24 | 3:30 PM | League | | | Depaolo Middle School - DMS Softball Field |
| FRI 5/24 | 3:30 PM | League | | | Wamogo Middle School Softball Field - Wamogo Regional Middle School Girls Softball |
| FRI 5/24 | 3:45 PM | League | | | Eliot MS - Softball Field |
| FRI 5/24 | 3:45 PM | League | | | West Side Middle School-Waterbury - Town Plot Park |
| FRI 5/24 | 4:00 PM | League | | | Polson MS - Green Hill Softball Field - Grass |
| FRI 5/24 | 4:00 PM | League | | | Portland MS - Rose Hill Field : 160 Rose Hill Rd Portland |
| FRI 5/24 | Canceled | League | | | City Hill Middle School - Softball field (Breen field) |
| FRI 5/24 | Canceled | League | | | North End Middle School - Bucks Hill Park |
| FRI 5/24 | Canceled | League | | | Tyrrell Middle School - Softball Field |
| TUE 5/28 | 3:30 PM | Postseason | Innovation MS | International MS | Chesley Park - Softball Diamond #1 |
| TUE 5/28 | 3:30 PM | Postseason | Aerospace/Engineering - Windsor | Comp Sci MS | LP Wilson - Softball Diamond |
| TUE 5/28 | 3:45 PM | League | | | Windsor Locks MS - Softball Field |
| TUE 5/28 | 3:45 PM | League | | | Winsted Rowley Field - Winsted Rowley Field |
| TUE 5/28 | 3:45 PM | Non-League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| TUE 5/28 | 3:45 PM | Postseason | | | Sage Park Middle School - Windsor High School |
| TUE 5/28 | 4:00 PM | League | | | Bethel Middle School - Johnson Field |
| TUE 5/28 | 4:00 PM | League | | | Cromwell Middle School - Cromwell High School |
| TUE 5/28 | 4:00 PM | League | | | Derby High School - Payden Park |
| TUE 5/28 | 4:00 PM | League | | | Helen Baldwin Middle School - BMS School Field |
| TUE 5/28 | 4:00 PM | League | | | Lisbon Central School - Default Facility |
| TUE 5/28 | 4:00 PM | League | | | Thomaston Center School - Sanford Field |
| TUE 5/28 | 4:15 PM | League | | | Greene Hills Elementary - Softball Field |
| TUE 5/28 | Postponed | League | | | Amity Middle School - Bethany - Softball Field |
| TUE 5/28 | Postponed | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| WED 5/29 | 3:30 PM | League | | | Litchfield High School - Softball Field |
| WED 5/29 | 3:30 PM | League | | | Schaghticoke MS - Schaghticoke MS |
| WED 5/29 | 3:30 PM | League | | | Thomaston Center School - Sanford Field |
| WED 5/29 | 3:30 PM | League | | | West Bristol School - Softball Field |
| WED 5/29 | 3:45 PM | League | | | Greene Hills Elementary - Softball Field |
| WED 5/29 | 3:45 PM | League | | | North Haven Athletic Complex - Brook Field-Softball |
| WED 5/29 | 3:45 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| WED 5/29 | 3:45 PM | League | | | Westbrook Middle School - Westbrook MS Field #4 - Softball |
| WED 5/29 | 3:45 PM | Non-League | | | Shelton Intermediate School - Intermediate - Softball diamond |
| WED 5/29 | 4:00 PM | League | | | Newtown MS - Softball Field |
| THU 5/30 | 3:45 PM | League | | | Washington Primary School - Washington Primary School Softball Field |
| THU 5/30 | 4:15 PM | League | | | Jockey Hollow - Wolfe Park Field 4 |
| THU 5/30 | Canceled | League | | | Bradley School - Bradley Field |
| THU 5/30 | Canceled | League | | | Schaghticoke MS - Schaghticoke MS |
| THU 5/30 | Canceled | League | | | Wallace Middle School - Crosby Softball Field |
| THU 5/30 | Postponed | League | | | Memorial Field - East Haven - Memorial Field |
| FRI 5/31 | 3:30 PM | League | | | ASHFORD SCHOOL - Softball Field |
| FRI 5/31 | 3:30 PM | Postseason | Innovation MS | Aerospace/Engineering - Windsor | Chesley Park - Softball Diamond #1 |
| FRI 5/31 | 3:45 PM | League | | | Woodbury Middle School - Softball Field |
| FRI 5/31 | 4:00 PM | League | | | Bethel Middle School - Johnson Field |
| FRI 5/31 | 4:00 PM | League | | | Chippens Hill Middle School - Softball Diamond |
| MON 6/3 | 3:30 PM | League | | | Thomaston Center School - Sanford Field |
| MON 6/3 | 3:30 PM | Postseason | | | Killingly Intermediate School - KIS Softball Field |
| MON 6/3 | 3:45 PM | Postseason | | | City Hill Middle School - Softball field (Breen field) |
| MON 6/3 | 4:00 PM | League | | | Torrington Middle School - Torrington Middle School Field #1 |
| TUE 6/4 | 3:30 PM | League | | | Thomaston Center School - Sanford Field |
| TUE 6/4 | 3:30 PM | League | | | Wamogo Middle School Softball Field - Wamogo Regional Middle School Girls Softball |
| TUE 6/4 | 4:00 PM | League | | | Rochambeau Middle School - RMS Softball Field |
| WED 6/5 | 3:30 PM | League | | | N W Regional 7 Middle School Girls Softball - N W Regional 7 Middle School Girls Softball Field |
| WED 6/5 | 3:45 PM | Postseason | | | Naugatuck High School - Softball Diamond |
| FRI 6/7 | 3:00 PM | League | | | Thomaston Center School - Sanford Field |