| 1 | 991 | 9/7/19 10:30am | English High School 7v7 | JP Dynamo | 0 - 1 | Brookline Juventus | |
| 2 | 994 | 9/14/19 3:15pm | Soule Recreation Center | Brookline Juventus | 1 - 1 | Winchester Revolution | |
| 3 | 998 | 9/21/19 1:00pm | Millennium Park C | Parkway United White | 2 - 2 | Brookline Juventus | |
| 4 | 1000 | 9/28/19 4:30pm | Soule Recreation Center | Brookline Juventus | 2 - 3 | Winchester Fireballs | |
| 5 | 1005 | 10/5/19 1:00pm | Teddy Ebersols Red Sox Field 7v7 (1) | Hill House United White | 4 - 3 | Brookline Juventus | |
| 6 | 1006 | 10/12/19 3:00pm | Soule Recreation Center | Brookline Juventus | 0 - 2 | JP Dynamo | |
| 7 | 1010 | 10/19/19 1:30pm | Lynch 7v7-3 | Winchester Revolution | 0 - 0 | Brookline Juventus | |
| 8 | 1012 | 10/26/19 3:00pm | Beaver Country Day School | Brookline Juventus | 3 - 2 | Parkway United White | |
| 9 | 1016 | 11/2/19 1:30pm | Lynch 7v7-2 | Winchester Fireballs | 2 - 0 | Brookline Juventus | |
| 10 | 1018 | 11/9/19 1:30pm | Beaver Country Day School | Brookline Juventus | 2 - 0 | Hill House United White | |
