| 1 | 2512 | 4/26/24 5:15pm | Chickering Field | D-S Raiders | 2 - 2 | Canton Boys Grade 5 United | |
| 2 | 2515 | 4/13/24 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 2 - 2 | Brookline Athletico | |
| 3 | 2519 | 4/13/24 9:15am | Friends 1 (9v9) | Foxboro Warriors 5B-Blue | 2 - 5 | Canton Boys Grade 5 United | Rescheduled to earlier |
| 4 | 2520 | 4/27/24 12:00pm | Sprague 2A | Wellesley Honey Badgers | 3 - 4 | Canton Boys Grade 5 United | |
| 5 | 2524 | 5/14/24 6:30pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 4 - 2 | Wayland Wolfpack | |
| 6 | 2527 | 5/11/24 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 2 - 2 | D-S Raiders | |
| 7 | 2531 | 5/18/24 1:30pm | Skyline Park | Brookline Athletico | 8 - 2 | Canton Boys Grade 5 United | |
| 8 | 2534 | 5/18/24 9:00am | Devoll 9v9 Field | Canton Boys Grade 5 United | 4 - 1 | Foxboro Warriors 5B-Blue | |
| 9 | 2536 | 6/1/24 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 5 - 2 | Wellesley Honey Badgers | |
| 10 | 2539 | 6/8/24 12:30pm | Alpine Field #2 | Wayland Wolfpack | 0 - 1 | Canton Boys Grade 5 United | |
