5th Boys · 5th Boys - Division 5 · 2020-21 · Milton
Rank 4 · Record 5-6 · Power 1156.9
| 2021-03-13 | D5W-Medfield (burman) | 23-26 |
| 2021-03-11 | D5S-Dighton-Rehoboth | 30-19 |
| 2021-03-06 | D4S-Easton (crossman) | 30-20 |
| 2021-02-27 | D5E-Canton (green) | 24-47 |
| 2021-02-21 | D5E-North Quincy (bernard) | 45-27 |
| 2021-02-14 | D4-Milton (black) | 21-30 |
| 2021-01-31 | D5E-Norwood (blue) | 23-13 |
| 2021-01-23 | D5E-West Roxbury (white) | 24-26 |
| 2021-01-17 | D5E-Bellingham | 24-26 |
| 2021-01-10 | D5E-Canton (green) | 17-46 |
| 2021-01-02 | D5E-North Quincy (bernard) | 51-11 |