| 1 | 2421 | 9/6/25 2:30pm | Wheelock - # 4 | Medfield Warriors 4B | - | Canton Boys Grade 4 United | |
| 2 | 2426 | 9/13/25 9:00am | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Parkway B4 United Blue | |
| 3 | 2432 | 9/20/25 3:30pm | Roxbury YMCA | SUP South End Red Bulls | - | Canton Boys Grade 4 United | |
| 4 | 2436 | 9/27/25 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Medfield United 4B | |
| 5 | 2444 | 10/4/25 3:00pm | Lynch 7v7-1 | Winchester Rapids | - | Canton Boys Grade 4 United | |
| 6 | 2446 | 10/11/25 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Medfield Warriors 4B | |
| 7 | 2452 | 10/18/25 1:00pm | | Parkway B4 United Blue | - | Canton Boys Grade 4 United | |
| 8 | 2456 | 10/25/25 2:30pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 United | - | SUP South End Red Bulls | |
| 9 | 2462 | 11/1/25 2:30pm | Wheelock - # 1 | Medfield United 4B | - | Canton Boys Grade 4 United | |
| 10 | 2466 | 11/8/25 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Winchester Rapids | |
