5th Boys · 5th Boys - Division 4 · 2020-21 · Winchester
Rank 6 · Record 3-7 · Power 1200.3
| 2021-03-07 | D5-Belmont (white) | 25-35 |
| 2021-02-28 | D4-Natick (white) | 34-16 |
| 2021-02-15 | D4-Dover Sherborn (blue) | 19-29 |
| 2021-02-14 | D4-Dover Sherborn (white) | 38-35 |
| 2021-02-07 | D4-Milton (black) | 25-41 |
| 2021-01-31 | D4-Blackstone-Millville | 27-31 |
| 2021-01-24 | Triton D2 | 33-38 |
| 2021-01-17 | D4-Arlington (maroon) | 20-38 |
| 2021-01-10 | D4-Natick (white) | 18-13 |
| 2021-01-03 | D4-Arlington (maroon) | 17-47 |