| 1 | 5003 | 4/6/24 4:30pm | Skyline Park | Brookline Santos | 3 - 2 | Medfield Warriors 8B | |
| 2 | 5005 | 5/11/24 9:00am | AC Turf | Arlington FC | - | Brookline Santos | |
| 3 | 5008 | 5/4/24 10:30am | Beaver Country Day School | Brookline Santos | - | Needham Cosmos | |
| 4 | 5011 | 4/27/24 10:35am | Kennedy Middle School | Natick United | - | Brookline Santos | |
| 5 | 5013 | 5/4/24 4:30pm | Skyline Park | Brookline Santos | - | Lexington Strikers | |
| 6 | 5018 | 5/11/24 4:00pm | Wheelock - # 1 | Medfield Warriors 8B | - | Brookline Santos | |
| 7 | 5021 | 5/18/24 4:30pm | Skyline Park | Brookline Santos | - | Arlington FC | |
| 8 | 5022 | Unscheduled | DeFazio #2 Founders Field | Needham Cosmos | - | Brookline Santos | |
| 9 | 5025 | 6/1/24 4:30pm | Skyline Park | Brookline Santos | - | Natick United | |
| 10 | 5030 | 6/8/24 1:30pm | Center Track Field | Lexington Strikers | - | Brookline Santos | |
