| 1 | 2011 | 9/8/18 1:00pm | PQ (1A) | Belmont B5-2 Condors | 1 - 2 | Holliston Hotspur (B5 Robie) | |
| 2 | 2015 | 9/15/18 1:00pm | HYSA Park M-3 | Holliston Hotspur (B5 Robie) | 0 - 4 | Medfield Warriors | |
| 3 | 2018 | 9/22/18 1:15pm | Lower Fields 2A | A-B United | 4 - 1 | Holliston Hotspur (B5 Robie) | |
| 4 | 2019 | 10/5/18 5:30pm | Hadley 1 (11v11) | Westborough United - B5 | 0 - 1 | Holliston Hotspur (B5 Robie) | looking to reschedule |
| 5 | 2023 | 9/28/18 5:00pm | HYSA Park M-2 | Holliston Hotspur (B5 Robie) | 3 - 4 | Walpole Wildcats | |
| 6 | 2026 | 10/13/18 1:00pm | HYSA Park M-3 | Holliston Hotspur (B5 Robie) | 2 - 4 | Belmont B5-2 Condors | |
| 7 | 2030 | 10/20/18 1:00pm | Wheelock - # 4 | Medfield Warriors | 4 - 1 | Holliston Hotspur (B5 Robie) | |
| 8 | 2033 | 11/4/18 2:30pm | HYSA Park M-3 | Holliston Hotspur (B5 Robie) | 2 - 3 | A-B United | |
| 9 | 2034 | 11/3/18 1:00pm | HYSA Park M-3 | Holliston Hotspur (B5 Robie) | 3 - 3 | Westborough United - B5 | |
| 10 | 2038 | 11/10/18 3:00pm | ZNorfolk Agricultural School 9v9 | Walpole Wildcats | 2 - 1 | Holliston Hotspur (B5 Robie) | |
