| 1 | 61 | 11/8/20 3:30pm | Flatley/Milton Healthcare | Milton Red Tide | 1 - 5 | Hill House United | Reschedule by 04_Oct2020 |
| 2 | 64 | 9/19/20 12:00pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United | 7 - 2 | Newton B Sporting | |
| 3 | 68 | 9/26/20 2:30pm | Warren C | Newton B Atletico | 2 - 7 | Hill House United | Ref:2-13; Lopsided Hill House |
| 4 | 70 | 10/3/20 12:00pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United | 4 - 5 | Milton Wizards | |
| 5 | 75 | 10/10/20 4:00pm | Flatley/Milton Healthcare | Milton Celestials | 0 - 5 | Hill House United | Ref: 0-6; Lopsided |
| 6 | 76 | 10/17/20 2:30pm | Flatley/Milton Healthcare | Milton Red Tide | 1 - 6 | Hill House United | Ref: 1-6 |
| 7 | 80 | 10/24/20 2:30pm | Warren A | Newton B Sporting | 1 - 3 | Hill House United | |
| 8 | 82 | 11/15/20 1:00pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United | 8 - 1 | Newton B Atletico | Lopsided: Hill House United |
| 9 | 86 | 11/8/20 2:00pm | Flatley/Milton Healthcare | Milton Wizards | 4 - 4 | Hill House United | |
| 10 | 88 | 11/14/20 12:00pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United | 9 - 6 | Milton Celestials | |
