| 1831 | 4/10/21 11:30am | DeFazio #3 Conroy | Needham Vipers | 0 - 2 | Wellesley Wolverines | |
| 1834 | 4/17/21 10:30am | Sprague 2A | Wellesley Wolverines | 2 - 0 | Natick All Stars | |
| 1838 | Unscheduled | Wheelock - 9v9-3 | Medfield Warriors 5G | - | Wellesley Wolverines | |
| 1840 | 5/1/21 12:00pm | Sprague 2A | Wellesley Wolverines | - | C-C Spirit | |
| 1845 | 5/8/21 11:35am | HYSA Park M-3 | Holliston G5 Predators BMalvey | - | Wellesley Wolverines | |
| 1846 | 5/15/21 10:30am | Sprague 3A | Wellesley Wolverines | - | Needham Vipers | |
| 1850 | 5/22/21 12:00pm | Cole North A (9v9) | Natick All Stars | - | Wellesley Wolverines | |
| 1852 | 5/29/21 11:45am | | Wellesley Wolverines | - | Medfield Warriors 5G | |
| 1856 | 6/5/21 11:45am | CCHS Turf 2A | C-C Spirit | - | Wellesley Wolverines | |
| 1858 | 6/12/21 12:00pm | Sprague 2A | Wellesley Wolverines | - | Holliston G5 Predators BMalvey | |
