| 603 | Unscheduled | Fruit St. Grass Field 5C | Hopkinton B4 Academy Orange | - | Canton Boys Grade 4 United | |
| 606 | Unscheduled | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Milf-Hopedale Raiders | |
| 609 | 4/24/21 1:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Franklin Panthers | |
| 612 | 5/1/21 1:00pm | Empire Masonry Field - 23 | Mansfield Mansfield Green Hornets | - | Canton Boys Grade 4 United | |
| 615 | 5/8/21 1:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Northborough Celtic | |
| 618 | 5/15/21 2:45pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Hopkinton B4 Academy Orange | |
| 619 | 5/22/21 1:00pm | Plains Park 7v7 Field #1 | Milf-Hopedale Raiders | - | Canton Boys Grade 4 United | |
| 624 | 5/29/21 1:00pm | Meadowlark | Franklin Panthers | - | Canton Boys Grade 4 United | |
| 627 | 6/5/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | - | Mansfield Mansfield Green Hornets | |
| 628 | 6/12/21 1:00pm | Ellsworth-McAfee Field 2 | Northborough Celtic | - | Canton Boys Grade 4 United | |
