| 1 | 2508 | 9/9/23 2:30pm | Weeks A | Newton B Flamengo | 1 - 0 | Canton Boys Grade 5 United | |
| 2 | 2511 | 9/16/23 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 3 - 3 | Holliston B5 - Aldredge/Looney | |
| 3 | 2514 | 9/23/23 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 1 - 3 | Dedham United | |
| 4 | 2517 | 9/30/23 12:45pm | Beaver Pond/Chilson Beach | Franklin Panthers | 2 - 2 | Canton Boys Grade 5 United | Ref entered score from wrong game |
| 5 | 2520 | 10/3/23 5:30pm | Gunning (Windsor Woods) 9v9 Field | Canton Boys Grade 5 United | 5 - 1 | Wellesley Honey Badgers | |
| 6 | 2523 | 10/14/23 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 4 - 0 | Newton B Flamengo | |
| 7 | 2524 | 10/21/23 2:30pm | HYSA Park M-2 | Holliston B5 - Aldredge/Looney | 0 - 4 | Canton Boys Grade 5 United | |
| 8 | 2529 | 10/28/23 1:00pm | Gonzalez Field | Dedham United | 4 - 2 | Canton Boys Grade 5 United | |
| 9 | 2532 | 11/4/23 10:15am | Pequitside Farm 9v9 Field | Canton Boys Grade 5 United | 0 - 2 | Franklin Panthers | |
| 10 | 2533 | 11/11/23 3:00pm | Elm Bank 3A | Wellesley Honey Badgers | 1 - 1 | Canton Boys Grade 5 United | |
