| 1 | 2912 | 9/6/25 11:45am | Arsenal 9v9 | Watertown Bears | 1 - 2 | Canton Boys Grade 5 Arsenal | |
| 2 | 2915 | 9/13/25 1:00pm | Gunning (Windsor Woods) 9v9 Field | Canton Boys Grade 5 Arsenal | - | Dorchester Lions 5B | |
| 3 | 2919 | 9/20/25 12:00pm | Rashi School (Grass) | Dedham Barracudas | - | Canton Boys Grade 5 Arsenal | |
| 4 | 2920 | 9/27/25 12:30pm | Grove St. (1A) | Belmont B5 Crew | - | Canton Boys Grade 5 Arsenal | |
| 5 | 2924 | 10/4/25 1:00pm | Gunning (Windsor Woods) 9v9 Field | Canton Boys Grade 5 Arsenal | - | Milton Wolves | |
| 6 | 2927 | 10/11/25 1:00pm | Gunning (Windsor Woods) 9v9 Field | Canton Boys Grade 5 Arsenal | - | Watertown Bears | |
| 7 | 2931 | 10/18/25 2:30pm | Pope John Paul II Park | Dorchester Lions 5B | - | Canton Boys Grade 5 Arsenal | |
| 8 | 2934 | 10/25/25 11:45am | Devoll 9v9 Field | Canton Boys Grade 5 Arsenal | - | Dedham Barracudas | |
| 9 | 2936 | 11/1/25 1:00pm | Gunning (Windsor Woods) 9v9 Field | Canton Boys Grade 5 Arsenal | - | Belmont B5 Crew | |
| 10 | 2939 | 11/8/25 2:40pm | Kelly Field | Milton Wolves | - | Canton Boys Grade 5 Arsenal | |
