| 1 | 2762 | 9/6/25 3:00pm | Mylod 2 | Walpole Arsenal | - | Canton Boys Grade 5 United | |
| 2 | 2765 | 9/13/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Milton Red Storm | |
| 3 | 2769 | 9/20/25 1:00pm | | Foxboro Warriors 5B-Blue | - | Canton Boys Grade 5 United | |
| 4 | 2770 | 9/27/25 1:00pm | | Parkway B5 United Blue | - | Canton Boys Grade 5 United | |
| 5 | 2774 | 10/4/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Winchester Eagles | |
| 6 | 2777 | 10/11/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Walpole Arsenal | |
| 7 | 2781 | 10/18/25 2:40pm | Point32Health Field | Milton Red Storm | - | Canton Boys Grade 5 United | |
| 8 | 2784 | 10/25/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Foxboro Warriors 5B-Blue | |
| 9 | 2786 | 11/1/25 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | - | Parkway B5 United Blue | |
| 10 | 2789 | 11/8/25 1:30pm | Field House Indoor 9v9-Front | Winchester Eagles | - | Canton Boys Grade 5 United | |
