5th Boys · 5th Boys - Division 4 · 2023-24 · Winchester
Rank 5 · Record 7-22 · Power 1276.8
| 2024-03-06 | D4C-Medford (blue) | 28-34 |
| 2024-03-03 | D5H-Bedford (white) | 39-20 |
| 2024-03-02 | D5H-Waltham Boys (white) | 32-29 |
| 2024-02-25 | D4D-Arlington (white) | 35-48 |
| 2024-02-18 | D4C-Natick | 27-29 |
| 2024-02-17 | D4D-Chelsea | 23-50 |
| 2024-02-17 | D4B-Hopkinton (mathot) | 36-59 |
| 2024-02-11 | D4D-Belmont (white) | 17-37 |
| 2024-02-10 | D4D-Lexington (blue) | 31-60 |
| 2024-02-04 | D4C-Newton (orange) | 24-63 |
| 2024-02-03 | D6D-Lexington (gold) | 22-26 |
| 2024-01-28 | D4D-Arlington (white) | 19-44 |
| 2024-01-28 | D4C-Hopkinton (sakakeeny) | 25-41 |
| 2024-01-27 | D4C-Hopkinton (pantera) | 18-53 |
| 2024-01-20 | D4D-Arlington (white) | 34-53 |
| 2024-01-14 | D4C-Medford (blue) | 29-24 |
| 2024-01-13 | D6C-Belmont (blue) | 24-25 |
| 2024-01-06 | D3C-Bedford (blue) | 18-35 |
| 2024-01-06 | D3C-Bedford (blue) | 14-47 |
| 2023-12-17 | D4D-Medford (white) | 42-24 |
| 2023-12-16 | D4D-Arlington (white) | 30-59 |
| 2023-12-10 | D4D-Lexington (blue) | 14-37 |
| 2023-12-09 | D6C-Belmont (blue) | 40-10 |
| 2023-12-03 | D3C-Bedford (blue) | 15-48 |
| 2023-12-02 | D5C-Concord-Carlisle (white) | 26-20 |
| 2023-11-26 | Reading (Guarino) (5B) | 25-29 |
| 2023-11-25 | Reading (Gaffen) (5B) | 16-28 |
| 2023-11-25 | Wilmington (White) (5A) | 30-22 |