| 1 | 2583 | 4/6/19 12:00pm | Skyline Park | Brookline Benfica | 4 - 0 | Natick Mad Men | |
| 2 | 2585 | 6/14/19 5:30pm | Teddy Ebersols Red Sox Field 9v9 (1) | Hill House United | 0 - 4 | Brookline Benfica | email me when the game is played |
| 3 | 2588 | 5/11/19 9:00am | Weston Middle School Field #9 | Weston Real Weston | 3 - 2 | Brookline Benfica | |
| 4 | 2591 | 5/7/19 5:45pm | Millennium Park C | Parkway United Blue | 1 - 1 | Brookline Benfica | Rain out - email me when the game is played |
| 5 | 2593 | 5/4/19 12:00pm | Skyline Park | Brookline Benfica | 1 - 0 | Milton Celtic | |
| 6 | 2598 | 5/11/19 2:30pm | Elm Bank Field 3A (9v9) | Natick Mad Men | 0 - 4 | Brookline Benfica | |
| 7 | 2601 | 5/18/19 12:00pm | Skyline Park | Brookline Benfica | 4 - 2 | Hill House United | |
| 8 | 2602 | 6/1/19 2:30pm | Weston Middle School Field #9 | Weston Real Weston | 1 - 0 | Brookline Benfica | |
| 9 | 2605 | 6/8/19 12:00pm | Skyline Park | Brookline Benfica | 1 - 0 | Parkway United Blue | |
| 10 | 2610 | 6/15/19 2:30pm | Andrews Field | Milton Celtic | F - 1 | Brookline Benfica | Milton Forfeited |
