8th Boys · 8th Boys - Division 5 · 2019-20 · Winchester
Rank 6 · Record 9-16 · Power 1055.7
| 2020-03-08 | D5N-Reading (red) | 29-32 |
| 2020-03-07 | D4N-Revere | 44-17 |
| 2020-03-01 | D5W-Northboro (white) | 35-65 |
| 2020-02-29 | D5W-Belmont (blue) | 36-41 |
| 2020-02-23 | D5W-Watertown (red) | 24-27 |
| 2020-02-16 | D5N-Arlington (white) | 39-40 |
| 2020-02-15 | D5N-Winchester (green) | 15-25 |
| 2020-02-09 | D5N-Winchester (green) | 30-41 |
| 2020-02-08 | D5W-Watertown (red) | 42-24 |
| 2020-02-02 | D5N-Reading (red) | 29-22 |
| 2020-02-01 | D3N-Bedford (blue) | 21-34 |
| 2020-01-26 | D5N-Andover | 38-49 |
| 2020-01-25 | D5N-Arlington (black) | 30-54 |
| 2020-01-19 | D5N-Reading (white) | 36-27 |
| 2020-01-18 | D5N-Reading (white) | 48-26 |
| 2020-01-12 | D5N-Arlington (black) | 33-48 |
| 2020-01-11 | D5W-Belmont (blue) | 40-33 |
| 2020-01-05 | D5W-Belmont (blue) | 26-30 |
| 2020-01-04 | D5N-Reading (red) | 31-28 |
| 2019-12-22 | D5N-Lexington | 43-58 |
| 2019-12-21 | D5N-Reading (red) | 32-33 |
| 2019-12-15 | D5W-Newton (white) | 29-50 |
| 2019-12-14 | D4N-Concord-Carlisle (white) | 17-50 |
| 2019-12-08 | D5W-Wayland | 27-17 |
| 2019-12-07 | D5N-Reading (red) | 30-21 |