| 1 | 931 | 9/11/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Arsenal | 6 - 2 | Holliston B4 Morrissey | |
| 2 | 936 | 9/18/21 1:00pm | Fruit St. Grass Field 5C | Hopkinton B4 Academy White | 0 - 3 | Canton Boys Grade 4 Arsenal | |
| 3 | 937 | 9/25/21 1:00pm | Idylbrook 7 v 7 - field 11 | Medway Mustangs | 1 - 5 | Canton Boys Grade 4 Arsenal | |
| 4 | 941 | 10/2/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Arsenal | 0 - 6 | Attleboro Panthers | |
| 5 | 944 | 10/12/21 6:30pm | Filippello Park - Arlington St. | Watertown WARRIORS | 1 - 1 | Canton Boys Grade 4 Arsenal | |
| 6 | 946 | 10/16/21 1:00pm | HYSA Park M-4 | Holliston B4 Morrissey | 0 - 4 | Canton Boys Grade 4 Arsenal | |
| 7 | 949 | 10/23/21 1:00pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Arsenal | 1 - 1 | Framingham Fire | |
| 8 | 953 | Unscheduled | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Arsenal | - | Medway Mustangs | |
| 9 | 955 | 11/6/21 4:05pm | MathWorks Upper (7v7) | Natick Bolts | 1 - 1 | Canton Boys Grade 4 Arsenal | |
| 10 | 959 | 11/13/21 1:00pm | Galvin Upper 7v7 Field | Canton Boys Grade 4 Arsenal | 2 - 3 | Watertown WARRIORS | |
