| 1 | 1473 | 4/10/21 9:00am | CCHS Turf 2A | C-C Phantoms | 6 - 3 | Canton Boys Grade 5 United | |
| 2 | 1476 | 6/7/21 6:00pm | Pequitside Farm 9v9 Field | Canton Boys Grade 5 United | 3 - 2 | Medway Medway Mustangs | game made up |
| 3 | 1479 | 4/24/21 1:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 2 - 1 | Ashland Sharks | |
| 4 | 1482 | 5/1/21 2:15pm | Multi-Purpose 9v9 Turf WHS | Westwood United | 3 - 1 | Canton Boys Grade 5 United | |
| 5 | 1485 | 5/21/21 5:00pm | Pequitside Farm 9v9 Field | Canton Boys Grade 5 United | 5 - 2 | Walpole Legends | |
| 6 | 1488 | 5/15/21 3:00pm | Devoll 9v9 Field | Canton Boys Grade 5 United | 1 - 3 | C-C Phantoms | |
| 7 | 1489 | 5/22/21 2:00pm | Idylbrook 9 v9 - Duplicate DO NOT USE | Medway Medway Mustangs | 1 - 1 | Canton Boys Grade 5 United | |
| 8 | 1494 | 5/17/21 6:30pm | Briasco Field | Ashland Sharks | 3 - 6 | Canton Boys Grade 5 United | |
| 9 | 1497 | 6/5/21 1:00pm | Pequitside Farm 9v9 Field | Canton Boys Grade 5 United | 2 - 4 | Westwood United | |
| 10 | 1498 | 6/12/21 1:00pm | S.M. Lorusso & Sons Athletic Complex Turf Field 2B (9v9) | Walpole Legends | 0 - 3 | Canton Boys Grade 5 United | |
