| 1711 | 4/10/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | 3 - 2 | Milton Strikers | |
| 1716 | 4/17/21 1:00pm | Idyllbrook 9 v9 | Medway Mustangs | 5 - 0 | Canton Boys Grade 5 Arsenal | |
| 1717 | 4/24/21 1:30pm | Cutting | Sudbury Strikers | - | Canton Boys Grade 5 Arsenal | |
| 1721 | 5/1/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | - | Watertown COBRAS | |
| 1724 | 5/8/21 1:00pm | Wheelock - 9v9-3 | Medfield Fire 5B | - | Canton Boys Grade 5 Arsenal | |
| 1726 | 5/15/21 2:00pm | Pierce Middle School | Milton Strikers | - | Canton Boys Grade 5 Arsenal | |
| 1729 | 5/22/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | - | Medway Mustangs | |
| 1733 | 5/29/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | - | Sudbury Strikers | |
| 1735 | 6/5/21 1:00pm | Arsenal | Watertown COBRAS | - | Canton Boys Grade 5 Arsenal | |
| 1739 | 6/12/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | - | Medfield Fire 5B | |
