| 1 | 6829 | 9/7/19 10:30am | Bates 1 | Wellesley Thunder | 0 - 6 | Wellesley Patriots | |
| 2 | 6834 | 9/14/19 10:30am | Sprague 2A | Wellesley Patriots | 4 - 0 | Winchester Royals | |
| 3 | 6840 | 9/21/19 10:30am | Ellsworth-McAfee Field B | Northborough Dynamoes | 0 - 6 | Wellesley Patriots | |
| 4 | 6844 | 9/28/19 10:15am | Belmont Day School - Far Field | Belmont G6-3 Ravens | 2 - 1 | Wellesley Patriots | |
| 5 | 6849 | 10/5/19 10:30am | Sprague 3B | Wellesley Patriots | 2 - 2 | Wrentham Wrevolution | |
| 6 | 6854 | 10/12/19 12:00pm | Sprague 3A | Wellesley Patriots | 1 - 0 | Wellesley Thunder | |
| 7 | 6860 | 10/19/19 9:00am | Ryan Connolly Field 9v9-Front | Winchester Royals | 1 - 1 | Wellesley Patriots | |
| 8 | 6865 | 10/26/19 10:30am | Sprague 2B | Wellesley Patriots | 1 - 1 | Bedford Blaze | |
| 9 | 6869 | 11/2/19 10:30am | Sprague 2A | Wellesley Patriots | 0 - 1 | Belmont G6-3 Ravens | |
| 10 | 6871 | 11/9/19 10:30am | Field 1 (9v9) | Wrentham Wrevolution | 1 - 2 | Wellesley Patriots | |
