| GameDate | Time | Type | Home School | Away School | Site |
| 04/09/2027 | 4:00 PM | Non-League | Danbury | Bethel | Danbury High School - V Baseball Field |
| 04/16/2027 | 4:00 PM | League | Darien | Norwalk | Darien High School - DHS Baseball - Varsity Field |
| 04/16/2027 | 4:00 PM | League | New Canaan | Danbury | New Canaan HS - Coppo Field |
| 04/16/2027 | 4:00 PM | League | St. Joseph | Stamford | St. Joseph High School - Baseball Diamond |
| 04/16/2027 | 4:00 PM | League | Trumbull | Westhill | Trumbull High School - Varsity Baseball Field |
| 04/16/2027 | 4:15 PM | League | Wilton | Fairfield Warde | Allen's Meadow - Baseball Diamond |
| 04/16/2027 | 4:30 PM | League | Ridgefield | Staples | Governor Field - Governor Field |
| 04/19/2027 | 4:00 PM | League | Danbury | Trumbull | Danbury High School - V Baseball Field |
| 04/19/2027 | 4:00 PM | League | Fairfield Warde | St. Joseph | Fairfield Warde High School - Baseball Diamond |
| 04/19/2027 | 4:00 PM | League | Greenwich | Fairfield Ludlowe | Greenwich High School - GHS Baseball Diamond |
| 04/19/2027 | 4:00 PM | League | Norwalk | Wilton | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 04/19/2027 | 4:00 PM | League | Staples | New Canaan | Staples High School - Baseball Diamond |
| 04/19/2027 | 4:00 PM | League | Westhill | Darien | Westhill High School - Varsity Baseball Field |
| 04/21/2027 | 4:00 PM | League | Greenwich | Fairfield Warde | Greenwich High School - GHS Baseball Diamond |
| 04/21/2027 | 4:00 PM | League | Fairfield Ludlowe | Trumbull | Kiwanis Field - Baseball Diamond |
| 04/21/2027 | 4:00 PM | League | St. Joseph | Danbury | St. Joseph High School - Baseball Diamond |
| 04/21/2027 | 4:00 PM | League | Stamford | Wilton | Stamford High School - SHS Baseball Diamond |
| 04/21/2027 | 4:00 PM | League | Staples | Westhill | Staples High School - Baseball Diamond |
| 04/21/2027 | 4:30 PM | League | Ridgefield | New Canaan | Governor Field - Governor Field |
| 04/23/2027 | 4:00 PM | League | Darien | Danbury | Darien High School - DHS Baseball - Varsity Field |
| 04/23/2027 | 4:00 PM | League | Fairfield Warde | Norwalk | Fairfield Warde High School - Baseball Diamond |
| 04/23/2027 | 4:00 PM | League | Fairfield Ludlowe | Stamford | Kiwanis Field - Baseball Diamond |
| 04/23/2027 | 4:00 PM | League | Trumbull | Staples | Trumbull High School - Varsity Baseball Field |
| 04/23/2027 | 4:15 PM | League | Wilton | Westhill | Allen's Meadow - Baseball Diamond |
| 04/23/2027 | 4:30 PM | League | Ridgefield | Greenwich | Governor Field - Governor Field |
| 04/26/2027 | 4:00 PM | League | Danbury | Staples | Danbury High School - V Baseball Field |
| 04/26/2027 | 4:00 PM | League | Darien | Fairfield Ludlowe | Darien High School - DHS Baseball - Varsity Field |
| 04/26/2027 | 4:00 PM | League | Fairfield Warde | Stamford | Fairfield Warde High School - Baseball Diamond |
| 04/26/2027 | 4:00 PM | League | Norwalk | Greenwich | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 04/26/2027 | 4:00 PM | League | New Canaan | St. Joseph | New Canaan HS - Coppo Field |
| 04/26/2027 | 4:00 PM | League | Trumbull | Ridgefield | Trumbull High School - Varsity Baseball Field |
| 04/28/2027 | 4:00 PM | League | Danbury | Norwalk | Danbury High School - V Baseball Field |
| 04/28/2027 | 4:00 PM | League | Greenwich | Darien | Greenwich High School - GHS Baseball Diamond |
| 04/28/2027 | 4:00 PM | League | Fairfield Ludlowe | Ridgefield | Kiwanis Field - Baseball Diamond |
| 04/28/2027 | 4:00 PM | League | Stamford | Trumbull | Stamford High School - SHS Baseball Diamond |
| 04/28/2027 | 4:00 PM | League | Staples | Fairfield Warde | Staples High School - Baseball Diamond |
| 04/28/2027 | 4:00 PM | League | Westhill | St. Joseph | Westhill High School - Varsity Baseball Field |
| 04/30/2027 | 4:00 PM | League | Darien | Stamford | Darien High School - DHS Baseball - Varsity Field |
| 04/30/2027 | 4:00 PM | League | Norwalk | Staples | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 04/30/2027 | 4:00 PM | League | New Canaan | Fairfield Ludlowe | New Canaan HS - Coppo Field |
| 04/30/2027 | 4:00 PM | League | St. Joseph | Ridgefield | St. Joseph High School - Baseball Diamond |
| 04/30/2027 | 4:00 PM | League | Westhill | Danbury | Westhill High School - Varsity Baseball Field |
| 04/30/2027 | 4:15 PM | League | Wilton | Greenwich | Allen's Meadow - Baseball Diamond |
| 05/03/2027 | 4:00 PM | League | Greenwich | Westhill | Greenwich High School - GHS Baseball Diamond |
| 05/03/2027 | 4:00 PM | League | Fairfield Ludlowe | Wilton | Kiwanis Field - Baseball Diamond |
| 05/03/2027 | 4:00 PM | League | New Canaan | Trumbull | New Canaan HS - Coppo Field |
| 05/03/2027 | 4:00 PM | League | Stamford | Norwalk | Stamford High School - SHS Baseball Diamond |
| 05/03/2027 | 4:00 PM | League | Staples | St. Joseph | Staples High School - Baseball Diamond |
| 05/03/2027 | 4:30 PM | League | Ridgefield | Darien | Governor Field - Governor Field |
| 05/05/2027 | 4:00 PM | League | Darien | St. Joseph | Darien High School - DHS Baseball - Varsity Field |
| 05/05/2027 | 4:00 PM | League | Fairfield Warde | New Canaan | Fairfield Warde High School - Baseball Diamond |
| 05/05/2027 | 4:00 PM | League | Norwalk | Ridgefield | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 05/05/2027 | 4:00 PM | League | Staples | Stamford | Staples High School - Baseball Diamond |
| 05/05/2027 | 4:00 PM | League | Westhill | Fairfield Ludlowe | Westhill High School - Varsity Baseball Field |
| 05/05/2027 | 4:15 PM | League | Wilton | Trumbull | Allen's Meadow - Baseball Diamond |
| 05/07/2027 | 4:00 PM | League | Greenwich | Staples | Greenwich High School - GHS Baseball Diamond |
| 05/07/2027 | 4:00 PM | League | Fairfield Ludlowe | Norwalk | Kiwanis Field - Baseball Diamond |
| 05/07/2027 | 4:00 PM | League | New Canaan | Wilton | New Canaan HS - Coppo Field |
| 05/07/2027 | 4:00 PM | League | Stamford | Danbury | Stamford High School - SHS Baseball Diamond |
| 05/07/2027 | 4:00 PM | League | Trumbull | Darien | Trumbull High School - Varsity Baseball Field |
| 05/07/2027 | 4:30 PM | League | Ridgefield | Fairfield Warde | Governor Field - Governor Field |
| 05/10/2027 | 4:00 PM | League | Danbury | Ridgefield | Danbury High School - V Baseball Field |
| 05/10/2027 | 4:00 PM | League | Fairfield Warde | Darien | Fairfield Warde High School - Baseball Diamond |
| 05/10/2027 | 4:00 PM | League | Greenwich | Stamford | Greenwich High School - GHS Baseball Diamond |
| 05/10/2027 | 4:00 PM | League | Norwalk | Trumbull | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 05/10/2027 | 4:00 PM | League | St. Joseph | Wilton | St. Joseph High School - Baseball Diamond |
| 05/10/2027 | 4:00 PM | League | Staples | Fairfield Ludlowe | Staples High School - Baseball Diamond |
| 05/10/2027 | 4:00 PM | League | Westhill | New Canaan | Westhill High School - Varsity Baseball Field |
| 05/12/2027 | 4:00 PM | League | Danbury | Greenwich | Danbury High School - V Baseball Field |
| 05/12/2027 | 4:00 PM | League | Darien | New Canaan | Darien High School - DHS Baseball - Varsity Field |
| 05/12/2027 | 4:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Warde High School - Baseball Diamond |
| 05/12/2027 | 4:00 PM | League | St. Joseph | Trumbull | St. Joseph High School - Baseball Diamond |
| 05/12/2027 | 4:00 PM | League | Westhill | Stamford | Westhill High School - Varsity Baseball Field |
| 05/12/2027 | 4:15 PM | League | Wilton | Ridgefield | Allen's Meadow - Baseball Diamond |
| 05/14/2027 | 4:00 PM | League | Darien | Wilton | Darien High School - DHS Baseball - Varsity Field |
| 05/14/2027 | 4:00 PM | League | Greenwich | St. Joseph | Greenwich High School - GHS Baseball Diamond |
| 05/14/2027 | 4:00 PM | League | Fairfield Ludlowe | Danbury | Kiwanis Field - Baseball Diamond |
| 05/14/2027 | 4:00 PM | League | New Canaan | Norwalk | New Canaan HS - Coppo Field |
| 05/14/2027 | 4:00 PM | League | Trumbull | Fairfield Warde | Trumbull High School - Varsity Baseball Field |
| 05/14/2027 | 4:30 PM | League | Ridgefield | Westhill | Governor Field - Governor Field |
| 05/17/2027 | 4:00 PM | League | Fairfield Warde | Danbury | Fairfield Warde High School - Baseball Diamond |
| 05/17/2027 | 4:00 PM | League | Fairfield Ludlowe | St. Joseph | Kiwanis Field - Baseball Diamond |
| 05/17/2027 | 4:00 PM | League | Norwalk | Westhill | Nathan Hale Middle School - Callahan Complex at Nathan Hale Upper |
| 05/17/2027 | 4:00 PM | League | New Canaan | Stamford | New Canaan HS - Coppo Field |
| 05/17/2027 | 4:00 PM | League | Trumbull | Greenwich | Trumbull High School - Varsity Baseball Field |
| 05/17/2027 | 4:15 PM | League | Wilton | Staples | Allen's Meadow - Baseball Diamond |
| 05/18/2027 | 4:00 PM | League | Danbury | Wilton | Danbury High School - V Baseball Field |
| 05/18/2027 | 4:00 PM | League | Greenwich | New Canaan | Greenwich High School - GHS Baseball Diamond |
| 05/18/2027 | 4:00 PM | League | St. Joseph | Norwalk | St. Joseph High School - Baseball Diamond |
| 05/18/2027 | 4:00 PM | League | Stamford | Ridgefield | Stamford High School - SHS Baseball Diamond |
| 05/18/2027 | 4:00 PM | League | Staples | Darien | Staples High School - Baseball Diamond |
| 05/18/2027 | 4:00 PM | League | Westhill | Fairfield Warde | Westhill High School - Varsity Baseball Field |
| 12/23/2026 | 2:00 PM | Non-League | Fairfield Warde | New Milford | Fairfield Warde High School - Baseball Diamond |