| 1 | 1281 | 4/12/25 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Bulldogs | - | Canton Boys Grade 4 Chelsea | |
| 2 | 1286 | 4/19/25 4:20pm | Flatley/Milton Healthcare | Milton Hotspurs | - | Canton Boys Grade 4 Bulldogs | |
| 3 | 1287 | 4/26/25 1:00pm | Flatley/Milton Healthcare | Milton Knights | - | Canton Boys Grade 4 Bulldogs | |
| 4 | 1291 | 5/3/25 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Bulldogs | - | Dedham Regulators | |
| 5 | 1294 | 5/10/25 1:00pm | Ellsworth-McAfee Field 3 | Northborough Blue (Boys 4) | - | Canton Boys Grade 4 Bulldogs | |
| 6 | 1296 | 5/17/25 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Chelsea | - | Canton Boys Grade 4 Bulldogs | |
| 7 | 1299 | 5/24/25 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Bulldogs | - | Milton Hotspurs | |
| 8 | 1303 | 5/31/25 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Bulldogs | - | Milton Knights | |
| 9 | 1305 | 6/7/25 2:30pm | Condon Park | Dedham Regulators | - | Canton Boys Grade 4 Bulldogs | |
| 10 | 1309 | 6/14/25 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Bulldogs | - | Northborough Blue (Boys 4) | |
