| 1 | 753 | 9/11/21 1:00pm | Merchant Road Field 5 | Framingham Watkins | 2 - 3 | Canton Boys Grade 4 United | |
| 2 | 756 | 9/18/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | 5 - 4 | Milford-Hopedale Fireballs | |
| 3 | 759 | 9/25/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | 2 - 2 | Dedham Devils | |
| 4 | 762 | 10/2/21 1:00pm | Meadowlark | Franklin Panthers | 2 - 1 | Canton Boys Grade 4 United | |
| 5 | 765 | 10/15/21 5:00pm | Galvin Upper 7v7 Field | Canton Boys Grade 4 United | 5 - 0 | Milton Red Tide | |
| 6 | 768 | 10/16/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | 2 - 1 | Framingham Watkins | |
| 7 | 769 | 10/23/21 1:00pm | Plains Park 7v7 Field #1 | Milford-Hopedale Fireballs | 0 - 3 | Canton Boys Grade 4 United | |
| 8 | 774 | 10/30/21 1:00pm | Field 2 (7v7) | Wrentham Wrockets | 2 - 3 | Canton Boys Grade 4 United | |
| 9 | 777 | 11/6/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 United | 2 - 2 | Franklin Panthers | |
| 10 | 778 | 11/13/21 1:00pm | Flatley/Milton Healthcare | Milton Celestials | 0 - 2 | Canton Boys Grade 4 United | |
