| 1 | 1597 | 9/9/23 1:00pm | Friends 1 (7v7) | Foxboro Warriors 4B-White | 2 - 7 | Canton Boys Grade 4 Chelsea | |
| 2 | 1600 | 9/16/23 4:00pm | Galvin Upper 7v7 Field | Canton Boys Grade 4 Chelsea | 3 - 6 | Westwood Commanders | |
| 3 | 1604 | 9/23/23 1:00pm | Connections Physical Therapy Field - 11 | Mansfield Hornets III | 3 - 2 | Canton Boys Grade 4 Chelsea | |
| 4 | 1605 | 9/30/23 2:40pm | Flatley/Milton Healthcare | Milton Hammers | 8 - 3 | Canton Boys Grade 4 Chelsea | Milton played down in 2nd half |
| 5 | 1609 | 10/7/23 2:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Chelsea | 5 - 0 | Canton Boys Grade 4 Dawgs | |
| 6 | 1612 | 10/14/23 2:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Chelsea | 6 - 5 | Foxboro Warriors 4B-White | |
| 7 | 1616 | 10/21/23 10:30am | Thurston B 7v7 | Westwood Commanders | 6 - 3 | Canton Boys Grade 4 Chelsea | |
| 8 | 1619 | 10/28/23 2:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Chelsea | 0 - 0 | Mansfield Hornets III | |
| 9 | 1621 | 11/4/23 2:30pm | Gunning (Windsor Woods) 7v7 Field | Canton Boys Grade 4 Chelsea | 8 - 2 | Southboro Timbers | |
| 10 | 1624 | 11/11/23 1:00pm | Pequitside Farm 7v7 Field | Canton Boys Grade 4 Dawgs | 1 - 3 | Canton Boys Grade 4 Chelsea | |
