5th Boys · 5th Boys - Division 3 · 2019-20 · Winchester
Rank 1 · Record 19-7 · Power 1969.6
| 2020-03-08 | D3E-Milford (red) | 53-24 |
| 2020-03-01 | D3W-Weston | 48-62 |
| 2020-02-29 | D2N-Woburn (black) | 56-53 |
| 2020-02-29 | D1N-Belmont (maroon) | 53-55 |
| 2020-02-22 | D3W-Framingham (white) | 39-7 |
| 2020-02-09 | D3W-Brookline (red) | 52-40 |
| 2020-02-09 | D3N-Watertown (white) | 50-10 |
| 2020-02-08 | D3N-Watertown (white) | 47-36 |
| 2020-02-08 | D3W-Southboro (maroon) | 39-24 |
| 2020-02-02 | D3W-Newton (orange) | 51-22 |
| 2020-02-01 | Manchester-Essex (Green) 5B D2B | 57-53 |
| 2020-02-01 | D3N-Lexington | 46-20 |
| 2020-01-26 | D3E-Milford (red) | 47-36 |
| 2020-01-25 | D3N-Medford (blue) | 52-24 |
| 2020-01-19 | D3N-Arlington (maroon) | 31-32 |
| 2020-01-18 | Wakefield (Merrimack Valley) (5B) | 56-24 |
| 2020-01-12 | D3N-Lexington | 37-43 |
| 2020-01-11 | Lynnfield 5B D1 | 41-42 |
| 2020-01-05 | D3N-Wayland | 47-26 |
| 2020-01-04 | D1N-Belmont (maroon) | 50-54 |
| 2019-12-22 | D3N-Watertown (white) | 42-24 |
| 2019-12-21 | D3N-Watertown (white) | 51-37 |
| 2019-12-15 | D3N-Medford (blue) | 48-33 |
| 2019-12-14 | D3N-Arlington (maroon) | 56-32 |
| 2019-12-08 | D3E-Millis (maroon) | 53-19 |
| 2019-12-07 | D2N-Woburn (black) | 39-41 |