5th Boys · 5th Boys - Division 3 · 2021-22 · Winchester
Rank 1 · Record 22-1 · Power 2060.7
| 2022-03-13 | D1-Franklin | 36-39 |
| 2022-03-12 | D2G-Milton (red) | 62-44 |
| 2022-03-05 | D2H-Lincoln-Sudbury (blue) | 49-26 |
| 2022-03-04 | D2H-Wellesley (a) | 42-25 |
| 2022-02-27 | D3J-Medford (white) | 45-32 |
| 2022-02-21 | D3J-Woburn (black) | 41-30 |
| 2022-02-20 | D3J-Arlington (maroon) | 43-32 |
| 2022-02-13 | D2G-Medfield (solomon) | 52-43 |
| 2022-02-13 | D3J-Revere | 45-19 |
| 2022-02-06 | D3H-Norwood (gold) | 43-27 |
| 2022-02-05 | D3J-Arlington (maroon) | 45-27 |
| 2022-02-05 | D3H-Milford (red) | 40-35 |
| 2022-01-23 | D3H-Framingham (navy) | 60-19 |
| 2022-01-22 | D3J-Medford (white) | 38-17 |
| 2022-01-08 | D3J-Lexington | 64-25 |
| 2022-01-02 | D3H-Milford (red) | 31-29 |
| 2021-12-19 | D3J-Medford (white) | 46-21 |
| 2021-12-18 | D2H-Belmont (maroon) | 71-44 |
| 2021-12-12 | D3J-Revere | 43-30 |
| 2021-12-05 | D4AJ-Newton (orange) | 70-14 |
| 2021-12-04 | D3J-Woburn (black) | 50-27 |
| 2021-11-20 | D4B-Dedham (white) | 46-9 |
| 2021-11-20 | D3H-Westwood (a) | 38-22 |