| 1 | 2431 | 4/6/19 12:00pm | Sprague 3A | Wellesley Thunder | 2 - 0 | Milton Leopards | |
| 2 | 2434 | 5/31/19 6:00pm | Flatley/Milton Healthcare | Milton Leopards | 0 - 4 | Newton G Storm | No game played, rain closure |
| 3 | 2438 | Unscheduled | Weston Middle School Field #7 | Weston Lions | 0 - 0 | Milton Leopards | Game rescheduled 5/18 @ 2:30 |
| 4 | 2440 | 4/27/19 11:45am | Andrews Field | Milton Leopards | 0 - 3 | Arlington Buckley | Game not played, fields closed |
| 5 | 2445 | 5/4/19 12:00pm | Sprague 2A | Wellesley Wave | 1 - 0 | Milton Leopards | |
| 6 | 2446 | 5/11/19 11:45am | Andrews Field | Milton Leopards | X - X | Wellesley Thunder | multiple attempts by both teams to play, but unable to get the game in. |
| 7 | 2450 | 5/18/19 11:45am | Weeks E | Newton G Storm | 3 - 2 | Milton Leopards | |
| 8 | 2452 | 6/1/19 11:45am | Andrews Field | Milton Leopards | 0 - 1 | Weston Lions | |
| 9 | 2456 | 6/8/19 12:00pm | McClennen Park 2 | Arlington Buckley | 3 - 0 | Milton Leopards | |
| 10 | 2458 | 6/15/19 11:45am | Andrews Field | Milton Leopards | 4 - 0 | Wellesley Wave | |
