| 1 | 2344 | 4/6/24 11:45am | HYSA Park M-4 | Holliston B4 - Looney/Levasseur | 0 - 2 | Wellesley Reds | |
| 2 | 2347 | 5/30/24 6:30pm | Elm Bank 1 | Wellesley Reds | - | Franklin Strikers | |
| 3 | 2352 | 6/6/24 6:00pm | Plains Park 7v7 Field #1 | Milford-Hopedale Bulldogs | - | Wellesley Reds | |
| 4 | 2354 | 4/27/24 12:00pm | Sprague 4A | Wellesley Reds | 0 - 4 | Southboro Crew | |
| 5 | 2357 | 5/4/24 3:30pm | Fruit St. Grass Field 5C | Hopkinton B4 Academy | 1 - 6 | Wellesley Reds | |
| 6 | 2364 | 5/11/24 10:30am | Sprague 1B | Wellesley Reds | 5 - 0 | Holliston B4 - Looney/Levasseur | |
| 7 | 2367 | 5/18/24 2:30pm | Meadowlark | Franklin Strikers | 0 - 5 | Wellesley Reds | |
| 8 | 2371 | 6/4/24 6:30pm | Elm Bank 1 | Wellesley Reds | - | Milford-Hopedale Bulldogs | |
| 9 | 2375 | 6/1/24 1:00pm | Ellsworth-McAfee Field 2 | Northborough Green (Boys 4) | - | Wellesley Reds | |
| 10 | 2378 | 6/8/24 12:00pm | Sprague 4C | Wellesley Reds | - | Natick Redhawks | |
