5th Boys · 5th Boys - Division 5 · 2021-22 · Winchester
Rank 6 · Record 5-12 · Power 1057.1
| 2022-03-05 | D5A-Bedford (blue) | 18-29 |
| 2022-02-27 | D5BL-Natick | 25-33 |
| 2022-02-26 | D5BM-Arlington (white) | 24-32 |
| 2022-02-13 | D5A-Watertown (white) | 26-30 |
| 2022-02-12 | D5BM-Woburn (orange) | 28-20 |
| 2022-02-11 | D5BM-Woburn (orange) | 23-33 |
| 2022-02-06 | D5BL-Weston | 28-24 |
| 2022-02-05 | D5BL-Southboro (white) | 22-40 |
| 2022-01-23 | D5BM-Waltham Boys (white) | 18-29 |
| 2022-01-16 | D5BM-Medford (blue) | 39-14 |
| 2022-01-15 | D4B-Belmont (white) | 28-22 |
| 2022-01-08 | D5BM-Lexington | 15-26 |
| 2021-12-19 | D5BM-Winchester (red) | 31-26 |
| 2021-12-18 | D4B-Belmont (white) | 19-43 |
| 2021-12-12 | D5BL-Wayland (black) | 30-57 |
| 2021-12-11 | D5A-Bedford (blue) | 26-29 |
| 2021-12-05 | D5BL-Northboro (white) | 15-27 |