| 1 | 33 | 9/7/19 2:30pm | Merchant Road Field 5 | Framingham Strikers | 2 - 1 | Brookline Red Bulls | |
| 2 | 36 | 9/14/19 11:30am | Soule Recreation Center | Brookline Red Bulls | 0 - 6 | Newton B Man United | Lopsided: Newton B M |
| 3 | 39 | 9/21/19 12:00pm | Soule Recreation Center | Brookline Red Bulls | 2 - 2 | Dedham Dedham FC | |
| 4 | 42 | 9/28/19 2:30pm | Flatley/Milton Healthcare | Milton Rovers | 6 - 0 | Brookline Red Bulls | |
| 5 | 45 | 10/5/19 12:00pm | Soule Recreation Center | Brookline Red Bulls | 2 - 2 | Weston Wildcats | |
| 6 | 76 | 10/12/19 12:00pm | Soule Recreation Center | Brookline Red Bulls | 4 - 2 | Hopkinton Galaxy | |
| 7 | 80 | 10/19/19 2:30pm | PJ Shannon Remodeling Field - 31 | Mansfield Green Hornets | 0 - 6 | Brookline Red Bulls | Lopsided: Brookline |
| 8 | 82 | 10/26/19 4:30pm | Soule Recreation Center | Brookline Red Bulls | 1 - 0 | Westborough United - B3 | |
| 9 | 86 | 11/2/19 2:30pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United | 2 - 2 | Brookline Red Bulls | |
| 10 | 88 | 11/9/19 10:30am | Beaver Country Day School | Brookline Red Bulls | 3 - 1 | Sudbury Warriors | |
