| GameDate | Time | Type | Home School | Away School | Site |
| 04/03/2027 | 11:00 AM | League | Simsbury | E.O. Smith | Memorial Park - Memorial Field #6 (Lighted) |
| 04/03/2027 | 12:00 PM | Non-League | Waterford | Glastonbury | Waterford High School - Veterans Softball Field - off campus |
| 04/03/2027 | 12:00 PM | League | Woodstock Academy | Stonington | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/03/2027 | 12:30 PM | League | Ledyard | Montville | Ledyard High School - Ellen Mahoney Softball Complex |
| 04/05/2027 | 3:45 PM | League | Berlin | Southington | Sage Park Berlin - Softball Field 2 |
| 04/05/2027 | 3:45 PM | League | E.O. Smith | Maloney | Mansfield Elementary School - Southeast Park: Field C |
| 04/05/2027 | 3:45 PM | League | East Hartford | Hall | East Hartford High School - Softball Diamond 2 |
| 04/05/2027 | 3:45 PM | League | Glastonbury | Bristol Eastern | Glastonbury High School - Field 9 |
| 04/05/2027 | 3:45 PM | League | Middletown | Manchester | Moody School - Upper Smith - Smith Park 2 - 300 Country Club Road, Middletown, CT |
| 04/05/2027 | 4:00 PM | League | Newington | Farmington | Newington High School - Softball Diamond 2 |
| 04/07/2027 | 3:45 PM | League | Bristol Central | Conard | South Side School - Softball Field |
| 04/07/2027 | 3:45 PM | League | Enfield | E.O. Smith | Enfield High School - EHS SOFTBALL JV |
| 04/07/2027 | 3:45 PM | League | Hall | Middletown | Hall High School - JV Softball |
| 04/07/2027 | 3:45 PM | League | Maloney | Berlin | Dunn Sports Complex - Dunn Sports Complex (pinwheel) |
| 04/07/2027 | 3:45 PM | League | Manchester | Newington | Charter Oak Park - Charter Oak Park |
| 04/07/2027 | 4:00 PM | League | Farmington | East Hartford | Tunxis Mead Park - JV Softball Field |
| 04/07/2027 | 4:00 PM | Non-League | Trumbull | Bethel | Trumbull High School - JV Softball Diamond |
| 04/07/2027 | 4:15 PM | League | Waterford | Bacon Academy | Waterford High School - Jody Nazarchyk Softball Field Turf |
| 04/07/2027 | 5:15 PM | League | Foran | Hillhouse | Foran High School - Danielle Kemp Memorial Field |
| 04/09/2027 | 3:45 PM | League | Berlin | Conard | Sage Park Berlin - Softball Field 2 |
| 04/09/2027 | 3:45 PM | League | Bristol Central | Maloney | South Side School - Softball Field |
| 04/09/2027 | 3:45 PM | League | Hall | Farmington | Hall High School - JV Softball |
| 04/09/2027 | 3:45 PM | League | Manchester | East Hartford | Charter Oak Park - Charter Oak Park |
| 04/09/2027 | 3:45 PM | League | Middletown | Newington | Moody School - Upper Smith - Smith Park 2 - 300 Country Club Road, Middletown, CT |
| 04/09/2027 | 3:45 PM | League | Southington | Bristol Eastern | Southington High School - 9 Softball JV Field |
| 04/09/2027 | 3:45 PM | League | Windsor | RHAM | Windsor High School - JV Softball Field |
| 04/09/2027 | 4:00 PM | League | Lakeview | Housatonic Regional | Lakeview High School - Lakeview JV Softball Field |
| 04/09/2027 | 4:15 PM | League | Woodstock Academy | New London | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/12/2027 | 12:00 PM | League | Woodstock Academy | Bacon Academy | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/12/2027 | 12:30 PM | Non-League | Canton | Coventry | Canton High School - Softball Diamond |
| 04/12/2027 | 3:45 PM | League | Bristol Central | Glastonbury | South Side School - Softball Field |
| 04/12/2027 | 3:45 PM | League | East Hartford | Newington | East Hartford High School - Softball Diamond 2 |
| 04/12/2027 | 3:45 PM | League | Enfield | Berlin | Enfield High School - EHS SOFTBALL JV |
| 04/12/2027 | 3:45 PM | League | Hall | Manchester | Hall High School - JV Softball |
| 04/12/2027 | 3:45 PM | League | Maloney | Southington | Dunn Sports Complex - Dunn Sports Complex (pinwheel) |
| 04/12/2027 | 3:45 PM | League | Platt | New Britain | Lincoln Middle School - Lincoln ms |
| 04/12/2027 | 3:45 PM | League | Simsbury | RHAM | Memorial Park - 90' Baseball Diamond (Lighted) |
| 04/12/2027 | 4:00 PM | League | Farmington | Middletown | Tunxis Mead Park - JV Softball Field |
| 04/12/2027 | 4:00 PM | League | Lakeview | Gilbert | Lakeview High School - Lakeview JV Softball Field |
| 04/12/2027 | 5:15 PM | League | Foran | Branford | Foran High School - Danielle Kemp Memorial Field |
| 04/13/2027 | 4:00 PM | Non-League | Norwalk | Shelton | Brookside Elementary School - Brookside Elementary School |
| 04/14/2027 | 3:45 PM | League | Bristol Eastern | Conard | Bristol Eastern High School - Page Park |
| 04/14/2027 | 3:45 PM | League | East Hartford | Middletown | East Hartford High School - Softball Diamond 2 |
| 04/14/2027 | 3:45 PM | League | Enfield | Maloney | Enfield High School - EHS SOFTBALL JV |
| 04/14/2027 | 3:45 PM | League | Southington | E.O. Smith | Southington High School - 9 Softball JV Field |
| 04/14/2027 | 3:45 PM | League | Windsor | New Britain | Windsor High School - JV Softball Field |
| 04/14/2027 | 4:00 PM | League | Farmington | Manchester | Tunxis Mead Park - JV Softball Field |
| 04/14/2027 | 4:00 PM | League | Ledyard | Bacon Academy | Ledyard High School - Ellen Mahoney Softball Complex |
| 04/14/2027 | 4:00 PM | League | Newington | Hall | Newington High School - Softball Diamond 2 |
| 04/15/2027 | 3:45 PM | League | Manchester | Avon | Charter Oak Park - Charter Oak Park |
| 04/15/2027 | 4:00 PM | Non-League | Norwalk | Bethel | Brookside Elementary School - Brookside Elementary School |
| 04/16/2027 | 12:00 PM | League | Woodstock Academy | Ledyard | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/16/2027 | 4:00 PM | League | Brien McMahon | Greenwich | Brookside Elementary School - Brookside Elementary School |
| 04/16/2027 | 4:00 PM | League | Fairfield Ludlowe | Bridgeport Central | Sturges Park (Ludlowe HS) - Softball Diamond |
| 04/16/2027 | 4:00 PM | League | Lakeview | Shepaug Valley | Lakeview High School - Lakeview JV Softball Field |
| 04/16/2027 | 4:00 PM | League | New Canaan | Danbury | Waveny Park - Orchard Field |
| 04/16/2027 | 4:00 PM | League | Trumbull | Westhill | Trumbull High School - JV Softball Diamond |
| 04/16/2027 | 4:00 PM | League | Wilton | Fairfield Warde | Wilton High School - JV Softball Field |
| 04/19/2027 | 3:45 PM | League | Berlin | E.O. Smith | Sage Park Berlin - Softball Field 2 |
| 04/19/2027 | 3:45 PM | League | Bristol Central | Bristol Eastern | South Side School - Softball Field |
| 04/19/2027 | 3:45 PM | League | Conard | Glastonbury | Sterling Field - Sterling Field #1 |
| 04/19/2027 | 3:45 PM | League | Enfield | Southington | Enfield High School - EHS SOFTBALL JV |
| 04/19/2027 | 3:45 PM | League | Simsbury | East Hartford | Memorial Park - 90' Baseball Diamond (Lighted) |
| 04/19/2027 | 3:45 PM | League | Windsor | Platt | Windsor High School - JV Softball Field |
| 04/19/2027 | 4:00 PM | League | Danbury | Trumbull | Danbury High School - JV Softball Field |
| 04/19/2027 | 4:00 PM | League | Ledyard | Plainfield | Ledyard High School - Ellen Mahoney Softball Complex |
| 04/19/2027 | 4:00 PM | League | Newington | RHAM | Newington High School - Softball Diamond 2 |
| 04/19/2027 | 4:00 PM | League | Norwalk | Wilton | Brookside Elementary School - Brookside Elementary School |
| 04/19/2027 | 4:00 PM | League | Stamford | Brien McMahon | Troy Complex - Diamond 1 |
| 04/19/2027 | 4:00 PM | League | Staples | New Canaan | Bedford Middle School - Wakeman Softball Field |
| 04/19/2027 | 4:15 PM | League | Woodstock Academy | St. Bernard | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/19/2027 | 4:30 PM | League | Greenwich | Fairfield Ludlowe | Julian Curtiss School - Baseball Diamond |
| 04/20/2027 | 4:00 PM | Non-League | Canton | Hall | Canton High School - Softball Diamond |
| 04/21/2027 | 3:45 PM | League | Berlin | Glastonbury | Sage Park Berlin - Softball Field 2 |
| 04/21/2027 | 3:45 PM | League | Bristol Eastern | Enfield | Bristol Eastern High School - Page Park |
| 04/21/2027 | 3:45 PM | League | E.O. Smith | Bristol Central | Mansfield Elementary School - Southeast Park: Field C |
| 04/21/2027 | 3:45 PM | League | Manchester | Platt | Charter Oak Park - Charter Oak Park |
| 04/21/2027 | 4:00 PM | League | Bridgeport Central | Norwalk | Cal Ripken Field - Longfellow Park |
| 04/21/2027 | 4:00 PM | League | Fairfield Ludlowe | Trumbull | Sturges Park (Ludlowe HS) - Softball Diamond |
| 04/21/2027 | 4:00 PM | League | Farmington | New Britain | Tunxis Mead Park - JV Softball Field |
| 04/21/2027 | 4:00 PM | League | Ledyard | Fitch | Ledyard High School - Ellen Mahoney Softball Complex |
| 04/21/2027 | 4:00 PM | League | Newington | Windsor | Newington High School - Softball Diamond 2 |
| 04/21/2027 | 4:00 PM | League | Stamford | Wilton | Troy Complex - Diamond 1 |
| 04/21/2027 | 4:00 PM | League | Staples | Westhill | Bedford Middle School - Wakeman Softball Field |
| 04/21/2027 | 4:15 PM | League | Waterford | Woodstock Academy | Waterford High School - Veterans Softball Field - off campus |
| 04/21/2027 | 4:30 PM | League | Greenwich | Fairfield Warde | Julian Curtiss School - Baseball Diamond |
| 04/22/2027 | 4:15 PM | League | Brookfield | Harding | Brookfield High School - BHS Softball Field |
| 04/23/2027 | 3:45 PM | League | Berlin | Newington | Sage Park Berlin - Softball Field 2 |
| 04/23/2027 | 3:45 PM | League | E.O. Smith | Manchester | Mansfield Elementary School - Southeast Park: Field C |
| 04/23/2027 | 3:45 PM | League | Platt | Southington | Lincoln Middle School - Lincoln ms |
| 04/23/2027 | 3:45 PM | League | RHAM | East Hartford | RHAM High School - Veterans Field |
| 04/23/2027 | 4:00 PM | League | Fairfield Ludlowe | Stamford | Sturges Park (Ludlowe HS) - Softball Diamond |
| 04/23/2027 | 4:00 PM | League | Fairfield Warde | Norwalk | Melville Park - Melville Park |
| 04/23/2027 | 4:00 PM | League | Farmington | Hall | Tunxis Mead Park - JV Softball Field |
| 04/23/2027 | 4:00 PM | League | New Canaan | Bridgeport Central | Waveny Park - Orchard Field |
| 04/23/2027 | 4:00 PM | League | Trumbull | Staples | Trumbull High School - JV Softball Diamond |
| 04/23/2027 | 4:00 PM | League | Wilton | Westhill | Wilton High School - JV Softball Field |
| 04/23/2027 | 4:00 PM | League | Woodstock Academy | Windham | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/23/2027 | 4:15 PM | League | Waterford | East Lyme | Waterford High School - Veterans Softball Field - off campus |
| 04/26/2027 | 3:45 PM | Non-League | E.O. Smith | Rockville | Mansfield Elementary School - Southeast Park: Field C |
| 04/26/2027 | 3:45 PM | Non-League | Ellington | Glastonbury | Ellington High School - Softball Diamond |
| 04/26/2027 | 4:00 PM | League | Danbury | Staples | Danbury High School - JV Softball Field |
| 04/26/2027 | 4:00 PM | League | Fairfield Warde | Stamford | Melville Park - Melville Park |
| 04/26/2027 | 4:00 PM | League | Lakeview | Nonnewaug | Lakeview High School - Lakeview JV Softball Field |
| 04/26/2027 | 4:00 PM | League | Norwalk | Greenwich | Brookside Elementary School - Brookside Elementary School |
| 04/26/2027 | 4:00 PM | League | Westhill | Bridgeport Central | Roxbury Elementary School - Softball Field |
| 04/26/2027 | 4:00 PM | League | Wilton | Brien McMahon | Wilton High School - JV Softball Field |
| 04/26/2027 | 4:15 PM | League | Woodstock Academy | Lyman Memorial | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 04/27/2027 | 3:45 PM | Non-League | RHAM | | RHAM High School - Veterans Field |
| 04/27/2027 | 4:15 PM | League | Brookfield | New Milford | Brookfield High School - BHS Softball Field |
| 04/28/2027 | 3:45 PM | League | Conard | Farmington | Sterling Field - Sterling Field #1 |
| 04/28/2027 | 3:45 PM | League | East Hartford | E.O. Smith | East Hartford High School - Softball Diamond 2 |
| 04/28/2027 | 3:45 PM | League | Glastonbury | Enfield | Glastonbury High School - Field 9 |
| 04/28/2027 | 3:45 PM | League | New Britain | Platt | Chesley Park - Chesley Park |
| 04/28/2027 | 3:45 PM | League | Simsbury | Bristol Central | Memorial Park - 90' Baseball Diamond (Lighted) |
| 04/28/2027 | 3:45 PM | League | Southington | Maloney | Southington High School - 9 Softball JV Field |
| 04/28/2027 | 4:00 PM | League | Bridgeport Central | Wilton | Cal Ripken Field - Longfellow Park |
| 04/28/2027 | 4:00 PM | League | Brien McMahon | New Canaan | Brookside Elementary School - Brookside Elementary School |
| 04/28/2027 | 4:00 PM | League | Danbury | Norwalk | Danbury High School - JV Softball Field |
| 04/28/2027 | 4:00 PM | League | Newington | Middletown | Newington High School - Softball Diamond 2 |
| 04/28/2027 | 4:00 PM | League | Stamford | Trumbull | Troy Complex - Diamond 1 |
| 04/28/2027 | 4:00 PM | League | Staples | Fairfield Warde | Bedford Middle School - Wakeman Softball Field |
| 04/28/2027 | 4:15 PM | League | Waterford | Ledyard | Waterford High School - Veterans Softball Field - off campus |
| 04/28/2027 | 5:15 PM | League | Foran | Sheehan | Foran High School - Danielle Kemp Memorial Field |
| 04/29/2027 | 6:00 PM | Non-League | Ellington | Enfield | Ellington High School - Softball Diamond |
| 04/30/2027 | 3:45 PM | League | Conard | Bristol Eastern | Sterling Field - Sterling Field #1 |
| 04/30/2027 | 3:45 PM | League | East Hartford | Windsor | East Hartford High School - Softball Diamond 2 |
| 04/30/2027 | 3:45 PM | League | Hall | Bristol Central | Hall High School - JV Softball |
| 04/30/2027 | 3:45 PM | League | Manchester | Enfield | Charter Oak Park - Charter Oak Park |
| 04/30/2027 | 3:45 PM | League | New Britain | Middletown | Chesley Park - Chesley Park |
| 04/30/2027 | 3:45 PM | League | Southington | Berlin | Southington High School - 9 Softball JV Field |
| 04/30/2027 | 4:00 PM | League | Fairfield Warde | Bridgeport Central | Melville Park - Melville Park |
| 04/30/2027 | 4:00 PM | League | New Canaan | Fairfield Ludlowe | Waveny Park - Orchard Field |
| 04/30/2027 | 4:00 PM | League | Norwalk | Staples | Brookside Elementary School - Brookside Elementary School |
| 04/30/2027 | 4:00 PM | League | Trumbull | Brien McMahon | Trumbull High School - JV Softball Diamond |
| 04/30/2027 | 4:00 PM | League | Westhill | Danbury | Roxbury Elementary School - Softball Field |
| 04/30/2027 | 4:00 PM | League | Wilton | Greenwich | Wilton High School - JV Softball Field |
| 05/01/2027 | 10:00 AM | League | Brookfield | Bethel | Brookfield High School - BHS Softball Field |
| 05/03/2027 | 3:45 PM | League | Glastonbury | Manchester | Glastonbury High School - Field 9 |
| 05/03/2027 | 3:45 PM | League | Maloney | New Britain | Dunn Sports Complex - Dunn Sports Complex (pinwheel) |
| 05/03/2027 | 3:45 PM | League | Platt | Newington | Lincoln Middle School - Lincoln ms |
| 05/03/2027 | 3:45 PM | League | RHAM | Windsor | RHAM High School - Veterans Field |
| 05/03/2027 | 3:45 PM | League | Simsbury | Hall | Memorial Park - 90' Baseball Diamond (Lighted) |
| 05/03/2027 | 4:00 PM | League | Bridgeport Central | Danbury | Cal Ripken Field - Longfellow Park |
| 05/03/2027 | 4:00 PM | League | Brien McMahon | Fairfield Warde | Brookside Elementary School - Brookside Elementary School |
| 05/03/2027 | 4:00 PM | League | Fairfield Ludlowe | Wilton | Sturges Park (Ludlowe HS) - Softball Diamond |
| 05/03/2027 | 4:00 PM | League | Lakeview | Thomaston | Lakeview High School - Lakeview JV Softball Field |
| 05/03/2027 | 4:00 PM | League | Ledyard | Killingly | Ledyard High School - Ellen Mahoney Softball Complex |
| 05/03/2027 | 4:00 PM | League | New Canaan | Trumbull | Waveny Park - Orchard Field |
| 05/03/2027 | 4:00 PM | League | Stamford | Norwalk | Troy Complex - Diamond 1 |
| 05/03/2027 | 4:15 PM | League | Waterford | Fitch | Waterford High School - Veterans Softball Field - off campus |
| 05/03/2027 | 4:30 PM | League | Greenwich | Westhill | Julian Curtiss School - Baseball Diamond |
| 05/04/2027 | 5:15 PM | League | Foran | Jonathan Law | Foran High School - Danielle Kemp Memorial Field |
| 05/05/2027 | 3:45 PM | League | Berlin | Maloney | Sage Park Berlin - Softball Field 2 |
| 05/05/2027 | 3:45 PM | League | Bristol Eastern | Simsbury | Bristol Eastern High School - Page Park |
| 05/05/2027 | 3:45 PM | League | E.O. Smith | RHAM | Mansfield Elementary School - Southeast Park: Field C |
| 05/05/2027 | 3:45 PM | League | Southington | Newington | Southington High School - 9 Softball JV Field |
| 05/05/2027 | 3:45 PM | League | Windsor | Glastonbury | Windsor High School - JV Softball Field |
| 05/05/2027 | 4:00 PM | League | Bridgeport Central | Greenwich | Cal Ripken Field - Longfellow Park |
| 05/05/2027 | 4:00 PM | League | Danbury | Brien McMahon | Danbury High School - JV Softball Field |
| 05/05/2027 | 4:00 PM | League | Fairfield Warde | New Canaan | Melville Park - Melville Park |
| 05/05/2027 | 4:00 PM | League | Staples | Stamford | Bedford Middle School - Wakeman Softball Field |
| 05/05/2027 | 4:00 PM | League | Westhill | Fairfield Ludlowe | Roxbury Elementary School - Softball Field |
| 05/05/2027 | 4:00 PM | League | Wilton | Trumbull | Wilton High School - JV Softball Field |
| 05/05/2027 | 4:00 PM | League | Woodstock Academy | Killingly | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 05/05/2027 | 4:15 PM | League | Waterford | NFA | Waterford High School - Veterans Softball Field - off campus |
| 05/06/2027 | 4:15 PM | League | Brookfield | Newtown | Brookfield High School - BHS Softball Field |
| 05/07/2027 | 4:00 PM | League | Brien McMahon | Westhill | Brookside Elementary School - Brookside Elementary School |
| 05/07/2027 | 4:00 PM | League | Fairfield Ludlowe | Norwalk | Sturges Park (Ludlowe HS) - Softball Diamond |
| 05/07/2027 | 4:00 PM | League | Ledyard | Woodstock Academy | Ledyard High School - Ellen Mahoney Softball Complex |
| 05/07/2027 | 4:00 PM | League | New Canaan | Wilton | Waveny Park - Orchard Field |
| 05/07/2027 | 4:00 PM | League | Stamford | Danbury | Troy Complex - Diamond 1 |
| 05/07/2027 | 4:30 PM | League | Greenwich | Staples | Julian Curtiss School - Baseball Diamond |
| 05/07/2027 | 5:15 PM | League | Foran | Lyman Hall | Foran High School - Danielle Kemp Memorial Field |
| 05/10/2027 | 3:45 PM | League | Conard | Bristol Central | Sterling Field - Sterling Field #1 |
| 05/10/2027 | 3:45 PM | League | East Hartford | Enfield | East Hartford High School - Softball Diamond 2 |
| 05/10/2027 | 3:45 PM | League | Glastonbury | E.O. Smith | Glastonbury High School - Field 9 |
| 05/10/2027 | 3:45 PM | League | Maloney | Middletown | Dunn Sports Complex - Dunn Sports Complex (pinwheel) |
| 05/10/2027 | 3:45 PM | League | New Britain | Berlin | Chesley Park - Chesley Park |
| 05/10/2027 | 3:45 PM | League | RHAM | Manchester | RHAM High School - Veterans Field |
| 05/10/2027 | 3:45 PM | League | Simsbury | Farmington | Memorial Park - 90' Baseball Diamond (Lighted) |
| 05/10/2027 | 4:00 PM | League | Bridgeport Central | Brien McMahon | Cal Ripken Field - Longfellow Park |
| 05/10/2027 | 4:00 PM | League | Lakeview | Northwestern | Lakeview High School - Lakeview JV Softball Field |
| 05/10/2027 | 4:00 PM | League | Norwalk | Trumbull | Brookside Elementary School - Brookside Elementary School |
| 05/10/2027 | 4:00 PM | League | Staples | Fairfield Ludlowe | Bedford Middle School - Wakeman Softball Field |
| 05/10/2027 | 4:00 PM | League | Westhill | New Canaan | Roxbury Elementary School - Softball Field |
| 05/10/2027 | 4:30 PM | League | Greenwich | Stamford | Julian Curtiss School - Baseball Diamond |
| 05/11/2027 | 5:15 PM | League | Foran | Mercy | Foran High School - Danielle Kemp Memorial Field |
| 05/12/2027 | 3:45 PM | League | Bristol Eastern | Farmington | Bristol Eastern High School - Page Park |
| 05/12/2027 | 3:45 PM | League | Enfield | RHAM | Enfield High School - EHS SOFTBALL JV |
| 05/12/2027 | 3:45 PM | League | Glastonbury | East Hartford | Glastonbury High School - Field 9 |
| 05/12/2027 | 3:45 PM | League | Middletown | Platt | Moody School - Upper Smith - Smith Park 2 - 300 Country Club Road, Middletown, CT |
| 05/12/2027 | 3:45 PM | League | Simsbury | Conard | Memorial Park - 90' Baseball Diamond (Lighted) |
| 05/12/2027 | 3:45 PM | League | Windsor | E.O. Smith | Windsor High School - JV Softball Field |
| 05/12/2027 | 4:00 PM | League | Danbury | Greenwich | Danbury High School - JV Softball Field |
| 05/12/2027 | 4:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Melville Park - Melville Park |
| 05/12/2027 | 4:00 PM | League | Newington | Maloney | Newington High School - Softball Diamond 2 |
| 05/12/2027 | 4:00 PM | League | Norwalk | Brien McMahon | Brookside Elementary School - Brookside Elementary School |
| 05/12/2027 | 4:00 PM | League | Staples | Bridgeport Central | Bedford Middle School - Wakeman Softball Field |
| 05/12/2027 | 4:00 PM | League | Westhill | Stamford | Roxbury Elementary School - Softball Field |
| 05/12/2027 | 4:15 PM | League | Waterford | Killingly | Waterford High School - Veterans Softball Field - off campus |
| 05/14/2027 | 3:45 PM | League | Bristol Eastern | Bristol Central | Bristol Eastern High School - Page Park |
| 05/14/2027 | 3:45 PM | League | Conard | Hall | Sterling Field - Sterling Field #1 |
| 05/14/2027 | 3:45 PM | League | East Hartford | Manchester | East Hartford High School - Softball Diamond 2 |
| 05/14/2027 | 3:45 PM | League | Maloney | Platt | Dunn Sports Complex - Dunn Sports Complex (pinwheel) |
| 05/14/2027 | 3:45 PM | League | Middletown | Berlin | Moody School - Upper Smith - Smith Park 2 - 300 Country Club Road, Middletown, CT |
| 05/14/2027 | 3:45 PM | League | New Britain | Southington | Chesley Park - Chesley Park |
| 05/14/2027 | 3:45 PM | League | Windsor | Enfield | Windsor High School - JV Softball Field |
| 05/14/2027 | 4:00 PM | League | Brien McMahon | Staples | Brookside Elementary School - Brookside Elementary School |
| 05/14/2027 | 4:00 PM | League | Fairfield Ludlowe | Danbury | Sturges Park (Ludlowe HS) - Softball Diamond |
| 05/14/2027 | 4:00 PM | League | Lakeview | ACES Chase Academy | Lakeview High School - Lakeview JV Softball Field |
| 05/14/2027 | 4:00 PM | League | New Canaan | Norwalk | Waveny Park - Orchard Field |
| 05/14/2027 | 4:00 PM | League | Stamford | Bridgeport Central | Troy Complex - Diamond 1 |
| 05/14/2027 | 4:00 PM | League | Trumbull | Fairfield Warde | Trumbull High School - JV Softball Diamond |
| 05/14/2027 | 4:30 PM | League | Greenwich | St. Joseph | Julian Curtiss School - Baseball Diamond |
| 05/14/2027 | 5:15 PM | League | Foran | Cheshire | Foran High School - Danielle Kemp Memorial Field |
| 05/15/2027 | 1:00 PM | League | Woodstock Academy | Putnam | The Woodstock Academy - North Campus - Town Commons Softball Diamond |
| 05/17/2027 | 3:45 PM | League | E.O. Smith | Enfield | Mansfield Elementary School - Southeast Park: Field C |
| 05/17/2027 | 3:45 PM | League | Hall | Bristol Eastern | Hall High School - JV Softball |
| 05/17/2027 | 3:45 PM | League | Manchester | Windsor | Charter Oak Park - Charter Oak Park |
| 05/17/2027 | 3:45 PM | League | New Britain | Newington | Chesley Park - Chesley Park |
| 05/17/2027 | 3:45 PM | League | Platt | Berlin | Lincoln Middle School - Lincoln ms |
| 05/17/2027 | 3:45 PM | League | RHAM | Glastonbury | RHAM High School - Veterans Field |
| 05/17/2027 | 3:45 PM | League | Southington | Middletown | Southington High School - 9 Softball JV Field |
| 05/17/2027 | 4:00 PM | League | Fairfield Warde | Danbury | Melville Park - Melville Park |
| 05/17/2027 | 4:00 PM | League | Farmington | Bristol Central | Tunxis Mead Park - JV Softball Field |
| 05/17/2027 | 4:00 PM | League | Ledyard | Waterford | Ledyard Middle School - Ledyard Middle School |
| 05/17/2027 | 4:00 PM | League | New Canaan | Stamford | Waveny Park - Orchard Field |
| 05/17/2027 | 4:00 PM | League | Norwalk | Westhill | Brookside Elementary School - Brookside Elementary School |
| 05/17/2027 | 4:00 PM | League | Trumbull | Greenwich | Trumbull High School - JV Softball Diamond |
| 05/17/2027 | 4:00 PM | League | Wilton | Staples | Wilton High School - JV Softball Field |
| 05/18/2027 | 3:45 PM | Non-League | E.O. Smith | Coventry | Mansfield Elementary School - Southeast Park: Field C |
| 05/18/2027 | 4:00 PM | League | Bridgeport Central | Trumbull | Cal Ripken Field - Longfellow Park |
| 05/18/2027 | 4:00 PM | League | Brien McMahon | Fairfield Ludlowe | Brookside Elementary School - Brookside Elementary School |
| 05/18/2027 | 4:00 PM | League | Danbury | Wilton | Danbury High School - JV Softball Field |
| 05/18/2027 | 4:00 PM | League | Westhill | Fairfield Warde | Roxbury Elementary School - Softball Field |
| 05/18/2027 | 4:15 PM | Non-League | Waterford | | Waterford High School - Veterans Softball Field - off campus |
| 05/18/2027 | 4:30 PM | League | Greenwich | New Canaan | Julian Curtiss School - Baseball Diamond |
| 05/20/2027 | 4:00 PM | Non-League | Canton | Berlin | Canton High School - Little League Softball Diamond |
| 05/20/2027 | 4:00 PM | League | Ledyard | Ellington | Ledyard Middle School - Ledyard Middle School |
| 05/21/2027 | 4:00 PM | Non-League | Ellington | Windsor | Ellington High School - Softball Diamond |
| 05/21/2027 | 4:00 PM | League | Ledyard | Southington | Ledyard Middle School - Ledyard Middle School |
| 05/21/2027 | 4:15 PM | League | Woodstock Academy | East Lyme | The Woodstock Academy - North Campus - Town Commons Softball Diamond |