| 09/09/2020 | Wilmington Wildcats | Royal | 5:00PM - 7:00PM | Beacon Street Fields / Cricklewood Field | |
| 09/09/2020 | Navy | Wilmington Nationals | 5:00PM - 7:00PM | Rotary / Rotary | |
| 09/09/2020 | Grey | Wilmington Red Sox | 5:00PM - 7:00PM | Boutwell / Boutwell | |
| 09/11/2020 | Royal | Grey | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/11/2020 | Navy | Woburn1 | 5:00PM - 7:00PM | Weafer / Weafer 1 | |
| 09/14/2020 | Wilmington Red Sox | Navy | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/14/2020 | Grey | Woburn2 | 5:00PM - 7:00PM | Weafer / Weafer 2 | |
| 09/16/2020 | Wilmington Nationals | Grey | 5:00PM - 7:00PM | Beacon Street Fields / Cricklewood Field | |
| 09/16/2020 | Woburn2 | Navy | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/21/2020 | Grey | Navy | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/21/2020 | Royal | Wilmington Red Sox | 5:00PM - 7:00PM | Boutwell / Boutwell | |
| 09/23/2020 | Woburn1 | Grey | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/23/2020 | Wilmington Wildcats | Navy | 5:00PM - 7:00PM | Beacon Street Fields / Cricklewood Field | |
| 09/23/2020 | Royal | Woburn2 | 5:00PM - 7:00PM | Weafer / Weafer 1 | |
| 09/25/2020 | Woburn1 | Royal | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | Rescheduled |
| 09/28/2020 | Navy | Royal | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/28/2020 | Grey | Wilmington Wildcats | 5:00PM - 7:00PM | Boutwell / Boutwell | |
| 09/30/2020 | Wilmington Red Sox | Grey | 5:00PM - 7:00PM | Beacon Street Fields / McCarthy Field | |
| 09/30/2020 | Wilmington Wildcats | Royal | 5:00PM - 7:00PM | Beacon Street Fields / Cricklewood Field | |
| 09/30/2020 | Navy | Wilmington Nationals | 5:00PM - 7:00PM | Rotary / Rotary | |
| 10/03/2020 | Royal | Wilmington Nationals | 1:00PM - 3:00PM | Rotary / Rotary | |