| 1 | 1891 | Unscheduled | Trottier Middle School - Track Infield | Southboro crew | X - X | Hopkinton B6 Academy Orange | |
| 2 | 1894 | 9/19/20 2:30pm | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | 6 - 1 | Northborough Knights | |
| 3 | 1898 | 9/26/20 2:30pm | Woodland School 9v9 Turf | Milford-Hopedale Hurricanes | 1 - 2 | Hopkinton B6 Academy Orange | |
| 4 | 1900 | 10/3/20 2:30pm | Fruit St. Turf Field 2B | Hopkinton B6 Academy Orange | 2 - 6 | Westborough Real - B6 | |
| 5 | 1905 | 10/10/20 1:30pm | HYSA Park M-3 | Holliston B6 Scaramella | 1 - 6 | Hopkinton B6 Academy Orange | |
| 6 | 1906 | 10/17/20 2:30pm | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | 0 - 5 | Southboro crew | |
| 7 | 1910 | 10/24/20 1:00pm | Ellsworth-McAfee Field B | Northborough Knights | 5 - 1 | Hopkinton B6 Academy Orange | |
| 8 | 1912 | Unscheduled | Fruit St. Turf Field 2A | Hopkinton B6 Academy Orange | X - X | Milford-Hopedale Hurricanes | |
| 9 | 1916 | 11/7/20 2:00pm | Chauncey 1 (9v9) | Westborough Real - B6 | 4 - 1 | Hopkinton B6 Academy Orange | |
| 10 | 1918 | 11/14/20 2:30pm | Fruit St. Turf Field 2B | Hopkinton B6 Academy Orange | 4 - 2 | Holliston B6 Scaramella | |
