| 1 | 1141 | 4/8/23 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Arsenal | 0 - 7 | Wellesley Inter | |
| 2 | 1144 | 4/14/23 4:45pm | Elm Bank 4 | Wellesley Inter | 0 - 5 | Newton B Gremio | |
| 3 | 1148 | 5/21/23 5:30pm | Flatley/Milton Healthcare | Milton Dynamo | 1 - 2 | Wellesley Inter | |
| 4 | 1150 | 4/29/23 12:00pm | Sprague 4A | Wellesley Inter | 1 - 1 | Dedham Falcons | |
| 5 | 1155 | 5/6/23 1:00pm | Laurel Farms | D-S Eagles | 1 - 2 | Wellesley Inter | |
| 6 | 1156 | 5/13/23 12:00pm | Sprague 1B | Wellesley Inter | 3 - 5 | Newton B Boca | |
| 7 | 1160 | 5/20/23 1:00pm | Fruit St. Grass Field 4B | Hopkinton B4 Academy | 1 - 5 | Wellesley Inter | |
| 8 | 1162 | 6/1/23 6:00pm | Elm Bank 4 | Wellesley Inter | 6 - 2 | Milton Dynamo | |
| 9 | 1166 | 6/3/23 2:30pm | Pool Field | Dedham Falcons | 4 - 2 | Wellesley Inter | |
| 10 | 1168 | 6/10/23 12:00pm | Sprague 4A | Wellesley Inter | 6 - 2 | Brookline Everton | |
