| 1 | 5670 | 9/8/18 10:30am | Fessenden B / Kumin-Loring | Newton G Blaze | 1 - 0 | Brookline Lions | |
| 2 | 5643 | 9/15/18 10:30am | Beaver Country Day School | Brookline Lions | 0 - 1 | Arlington Avalanche | |
| 3 | 5646 | 9/22/18 10:30am | Skillings Grass 11v11 | Winchester Revolution | 2 - 4 | Brookline Lions | |
| 4 | 5649 | 9/29/18 10:30am | Beaver Country Day School | Brookline Lions | 0 - 0 | Belmont G8-4 Hurricanes | |
| 5 | 5652 | 10/14/18 3:00pm | Center Track Field | Lexington Leopards | 1 - 0 | Brookline Lions | |
| 6 | 5655 | 10/13/18 12:00pm | Skyline Park | Brookline Lions | 0 - 1 | Newton G Blaze | |
| 7 | 5658 | 10/20/18 12:30pm | Peirce Field (HS turf) | Arlington Avalanche | 1 - 0 | Brookline Lions | |
| 8 | 5661 | 11/5/18 6:30pm | Ryan Connolly Field 11v11 | Winchester Revolution | 1 - 1 | Brookline Lions | make up game scheduled for 11/5 |
| 9 | 5664 | Unscheduled | Grove St. (4A) | Belmont G8-4 Hurricanes | X - X | Brookline Lions | Game was rained out, need to reschedule |
| 10 | 5667 | 11/10/18 10:30am | Beaver Country Day School | Brookline Lions | 0 - 5 | Lexington Leopards | |
