| Tuesday, May 21 |
| Montalvo Division |
| South Shore Giants @ Hyde Park Braves | 8:00pm | Kelley Field |
| Watertown Nationals @ Boston Cardinals | 8:00pm | Victory Field |
| Brockton Dodgers @ North Andover Thunder | 8:15pm | Bowzer Field (Clancy) |
| Wednesday, May 22 |
| Montgomery Division |
| Boston Astros @ Norwood Red Sox | 8:00pm | Barnes Memorial Park |
| Thursday, May 23 |
| Montalvo Division |
| North Shore Reds @ Waltham Cubs | 8:00pm | Barnes Memorial Park |
| Norwood Red Sox @ North Andover Thunder | 8:15pm | Bowzer Field (Clancy) |
| Montgomery Division |
| Hyde Park Braves @ Watertown Nationals | 8:00pm | Victory Field |
| Saturday, May 25 |
| Montalvo Division |
| Hyde Park Braves @ Waltham Cubs | 7:30pm | Nipper Maher Field |
| Tuesday, May 28 |
| Montalvo Division |
| Boston Astros @ North Shore Reds | 8:00pm | Bowzer Field (Clancy) |
| Braintree Rockies @ Hyde Park Braves | 8:00pm | Kelley Field |
| Montgomery Division |
| Norwood Red Sox @ Watertown Nationals | 8:00pm | Victory Field |
| Wednesday, May 29 |
| Doubleday Division - North |
| Waltham Braves @ Montgomery Blue Jays | 7:45pm | Nipper Maher Field |
| Montgomery Division |
| Brockton Dodgers @ Braintree Rockies | 7:30pm | Braintree High School |
| Boston Cardinals @ Brockton Athletics | 8:00pm | Barnes Memorial Park |
| Fenway Division |
| Mudville Nine Braves @ Gashouse Gang Royals | 8:00pm | Jefferson Field |
| Thursday, May 30 |
| Montalvo Division |
| South Shore Giants @ North Shore Reds | 8:00pm | Bowzer Field (Clancy) |
| Watertown Nationals @ North Andover Thunder | 8:00pm | Victory Field |
| Friday, May 31 |
| Fenway Division |
| San Luis Rays @ Duxbury Cardinals | 7:30pm | Braintree High School |
| Saturday, Jun 1 |
| Doubleday Division - North |
| Quincy Fours @ Waltham Braves | 7:45pm | Nipper Maher Field |
| Montgomery Division |
| Brockton Dodgers @ Brockton Athletics | 4:00pm | Gilmore School |
| North Andover Thunder @ South Shore Giants | 5:15pm | Libby Field |
| Sunday, Jun 2 |
| Doubleday Division - North |
| South Shore Hawks @ Montgomery Blue Jays | 4:00pm | Iacono Field |
| Scituate Mariners @ North Shore Thunder | 4:00pm | North Reading HS |
| Doubleday Division - South |
| Winchester Chiefs @ Cambridge Eagles | 9:00am | Rindge Field |
