| Opponent | Location | Date | Results |
| Medway (Scrimmage) | Hopedale (Blackstone Valley) | Sat, Dec 7, 2019 | W, 7-0 |
| Northbridge (Garrett Reagan) | Marlboro (NE Sports Center) | Sun Dec 8, 2019 | T, 1-1 |
| Silver Lake (SP&FT) | Hobomock | Sat, Dec 14, 2019 | W, 3-0 |
| Norwell (Old Oaken Bucket) | Hobomock | Sun, Dec 15, 2019 | T, 2-2 |
| Plymouth South | Armstrong Arena | Wed, Dec 18, 2019 | L, 4-3 |
| Marshfield | Hobomock | Sat, Dec 21, 2019 | L, 4-2 |
| SEWB | Raynham IcePlex | Thu, Dec 26, 2019 | W, 4-1 |
| Cohasset (Breen Cup) | Hobomock | Sat, Dec 28, 2019 | W, 5-1 |
| North Quincy | Quincy Youth Arena | Thu, Jan 2, 2020 | W, 5-1 |
| Coyle Cassidy | Hobomock | Sat, Jan 4, 2020 | W, 5-0 |
| North Quincy | Hobomock | Wed, Jan 8, 2020 | W, 4-3 |
| Pembroke | Hobomock | Sat, Jan 11, 2020 | W, 4-1 |
| Concord-Carlisle | THE BOG | Mon, Jan 20, 2020 | L, 2-1 |
| Plymouth North | Armstrong Arena | Wed, Jan 22, 2020 | L, 2-1 |
| Plymouth South | Hobomock | Sat, Jan 25, 2020 | W, 9-1 |
| Barnstable | Hyannis | Wed, Jan 29, 2020 | L, 7-2 |
| Pembroke | Hobomock | Sat, Feb 1, 2020 | W, 8-1 |
| Whitman-Hanson | Hobomock | Sun, Feb 2, 2020 | L, 4-1 |
| Hanover | Hobomock | Wed, Feb 5, 2020 | L, 3-0 |
| Duxbury | THE BOG | Sat, Feb 8, 2020 | L, 3-1 |
| Attleboro | NESV #2 | Wed, Feb 12, 2020 | W, 7-1 |
| Quincy | Hobomock | Sat, Feb 15, 2020 | W, 2-0 |
| Hanover (Gould Memorial Tournament) | Hobomock | Mon, Feb 17, 2020 | L, 3-0 |
| Pembroke (Gould Memorial Tourney) | Hobomock | Wed, Feb 19, 2020 | W, 7-0 |
| Playoff Game – S/WB | Gallo Arena | Wed, Feb 26, 2020 | W, 7-3 |
