5th Boys · 5th Boys - Division 5 · 2025-26 · Winchester
Rank 2 · Record 18-4 · Power 1470.3
| 2026-03-07 | D4Q-Medford (blue) | 30-38 |
| 2026-03-01 | D5W-Wayland (orange) | 31-34 |
| 2026-02-28 | D5T-Framingham (white) | 30-24 |
| 2026-02-28 | D6Q-Somerville (blue) | 41-22 |
| 2026-02-22 | D4M-Natick | 25-20 |
| 2026-02-15 | D4Q-Watertown (white) | 30-46 |
| 2026-02-08 | D5T-Lincoln-Sudbury (white) | 30-28 |
| 2026-02-07 | D4Q-Arlington (white) | 28-27 |
| 2026-02-01 | D5T-Weston | 49-9 |
| 2026-01-31 | D6R-Lexington (white) | 47-17 |
| 2026-01-24 | D6R-Bedford (white) | 19-34 |
| 2026-01-18 | D5W-Arlington (grey) | 40-21 |
| 2026-01-11 | D5W-Lexington (gold) | 37-11 |
| 2026-01-10 | D6R-Bedford (white) | 41-13 |
| 2026-01-04 | D5W-Waltham Boys (white) | 37-15 |
| 2026-01-03 | D5W-Arlington (grey) | 39-23 |
| 2025-12-21 | D5W-Belmont (white) | 27-18 |
| 2025-12-20 | D5W-Lexington (gold) | 35-4 |
| 2025-12-14 | D5W-Medford (white) | 60-7 |
| 2025-12-13 | D6Q-Watertown (red) | 46-17 |
| 2025-12-07 | D5T-Westborough | 40-37 |
| 2025-12-06 | D5W-Arlington (grey) | 33-14 |