| 1 | 4351 | 9/11/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 3 - 2 | Westborough United - B8 | |
| 2 | 4356 | 9/18/21 3:00pm | King Philip Middle School- Field 2 | King Philip Warriors Boys | 0 - 7 | Canton Boys Grade 7/8 United | |
| 3 | 4357 | 9/25/21 12:00pm | Poncin Hewitt | Attleboro Coyotes | 2 - 3 | Canton Boys Grade 7/8 United | |
| 4 | 4361 | 10/2/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 2 - 1 | Hopkinton Hillers (B8) | |
| 5 | 4364 | 10/29/21 6:30pm | Fessenden B/Kumin-Loring | Newton B FC | 0 - 6 | Canton Boys Grade 7/8 United | |
| 6 | 4366 | 10/16/21 2:30pm | Upper Haskell 1 (11v11) | Westborough United - B8 | 4 - 2 | Canton Boys Grade 7/8 United | |
| 7 | 4369 | 10/23/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 3 - 2 | Weston United | |
| 8 | 4373 | 10/30/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 1 - 0 | Attleboro Coyotes | |
| 9 | 4375 | 11/17/21 6:00pm | High School Turf Field | Hopkinton Hillers (B8) | 0 - 4 | Canton Boys Grade 7/8 United | |
| 10 | 4379 | 11/13/21 1:00pm | Memorial 11v11 Field (turf) | Canton Boys Grade 7/8 United | 1 - 0 | Newton B FC | |
