5th Boys · 5th Boys - Division 2 · 2020-21 · Winchester
Rank 2 · Record 6-6 · Power 1774.3
| 2021-03-13 | D1-Attleboro | 35-44 |
| 2021-03-07 | D2-Westborough | 33-32 |
| 2021-03-06 | D2-Waltham Boys | 38-27 |
| 2021-02-28 | D2-Natick (red) | 36-46 |
| 2021-02-21 | D3W-Medfield (huther) | 15-36 |
| 2021-02-14 | D2-Waltham Boys | 34-42 |
| 2021-02-07 | D2-Belmont (maroon) | 42-44 |
| 2021-01-31 | D2-Natick (red) | 32-27 |
| 2021-01-24 | D3-Southboro (maroon) | 44-34 |
| 2021-01-17 | D2-West Roxbury (red) | 46-23 |
| 2021-01-10 | D2-Waltham Boys | 30-26 |
| 2021-01-03 | D2-Belmont (maroon) | 33-40 |