| 2493 | 4/10/21 1:00pm | Trottier Middle School - Track Infield | Southboro crew | 1 - 1 | Mansfield Mansfield Hornets II | |
| 2495 | Unscheduled | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | - | Southboro crew | |
| 2498 | 4/24/21 1:00pm | Trottier Middle School - Track Infield | Southboro crew | - | Northborough Knights | |
| 2501 | 5/1/21 12:00pm | Poncin Hewitt | Attleboro Road Runners | - | Southboro crew | |
| 2503 | 5/8/21 11:00am | Choate 2 | Southboro crew | - | Framingham Storm | |
| 2508 | 5/15/21 2:30pm | PJ Shannon Remodeling Field - 21 | Mansfield Mansfield Hornets II | - | Southboro crew | |
| 2511 | 5/22/21 1:00pm | Trottier Middle School - Track Infield | Southboro crew | - | Hopkinton B6 Academy Orange | |
| 2512 | 5/29/21 2:30pm | Ellsworth-McAfee Field A | Northborough Knights | - | Southboro crew | |
| 2515 | 6/5/21 11:00am | Choate 2 | Southboro crew | - | Attleboro Road Runners | |
| 2520 | 6/12/21 3:00pm | Merchant Road Field 3 | Framingham Storm | - | Southboro crew | |
