5th Boys · 5th Boys - Division 3 · 2025-26 · Winchester
Rank 4 · Record 9-12 · Power 1785.5
| 2026-03-08 | D3K-Wellesley ((a)) | 18-35 |
| 2026-03-07 | D3K-Brookline (red) | 39-36 |
| 2026-03-01 | D3K-Arlington (maroon) | 29-37 |
| 2026-02-22 | D3J-Parkway (red) | 45-36 |
| 2026-02-08 | D3K-Lincoln-Sudbury (blue) | 40-34 |
| 2026-02-07 | D3K-Arlington (maroon) | 42-43 |
| 2026-02-01 | D3J-Medway (blue) | 36-38 |
| 2026-01-31 | D3K-Wellesley ((a)) | 30-52 |
| 2026-01-25 | D3J-Milton (white) | 36-39 |
| 2026-01-24 | D2M-Belmont (maroon) | 27-35 |
| 2026-01-18 | D3K-Brookline (red) | 45-41 |
| 2026-01-11 | D3J-Medfield (allen) | 32-38 |
| 2026-01-10 | D4Q-Lexington (blue) | 35-58 |
| 2026-01-03 | D3J-Norwood (gold) | 40-34 |
| 2026-01-03 | D3K-Arlington (maroon) | 31-37 |
| 2025-12-21 | D3K-Newton (orange) | 36-25 |
| 2025-12-20 | D2M-Bedford (blue) | 26-38 |
| 2025-12-14 | D3J-Westwood | 21-30 |
| 2025-12-13 | D2M-Belmont (maroon) | 39-35 |
| 2025-12-07 | D4M-Framingham (navy) | 31-19 |
| 2025-12-06 | D4Q-Watertown (white) | 42-32 |