| Date & Time | Division | Home | Away |
|---|---|---|---|
| February 22, 2019 | MIAA Boys | (0) Winchester Sachems | (2) Andover Golden Warriors |
| February 22, 2019 | ISL | (2) Thayer Academy (boys) | (3) St. Sebastian's (boys) |
| February 22, 2019 | MIAA Boys | (1) Lowell Red Raiders | (7) Triton Vikings |
| February 22, 2019 | ISL | (0) Thayer Academy (girls) | (3) BB&N (girls) |
| February 21, 2019 | MIAA Boys | (3) BC High Eagles | (0) Hingham Harbormen |
| February 21, 2019 | MIAA Boys | (1) Archbishop Williams Bishops | (1) Reading Rockets |
| February 20, 2019 | MIAA Boys | (4) Hanover Indians | (1) Scituate Sailors |
| February 20, 2019 | MIAA Boys | (0) Duxbury Dragons | (2) Austin Prep Cougars |
| February 20, 2019 | MIAA Boys | (4) Pembroke Titans | (6) Norwell Clippers |
| February 20, 2019 | MIAA Boys | (7) Falmouth Clippers | (3) Arlington Catholic Cougars |
| February 19, 2019 | MIAA Boys | (1) Newburyport Clippers | (3) Winchester Sachems |
| February 19, 2019 | MIAA Boys | (4) Andover Golden Warriors | (2) St. John's Shrewsbury Pioneers |
| February 18, 2019 | MIAA Boys | (0) Austin Prep Cougars | (2) BC High Eagles |
| February 18, 2019 | MIAA Boys | (9) Arlington Spy Ponders | (3) Andover Golden Warriors |
| February 18, 2019 | MIAA Boys | (3) Hingham Harbormen | (1) Duxbury Dragons |
| February 18, 2019 | MIAA Boys | (1) Falmouth Clippers | (2) Reading Rockets |
| February 18, 2019 | MIAA Boys | (0) Norwell Clippers | (4) Scituate Sailors |
| February 18, 2019 | MIAA Boys | (1) Arlington Catholic Cougars | (3) Archbishop Williams Bishops |
| February 18, 2019 | MIAA Boys | (3) Pembroke Titans | (4) Hanover Indians |
| February 16, 2019 | MIAA Boys | (0) Falmouth Clippers | (4) BC High Eagles |
| February 16, 2019 | MIAA Boys | (1) Reading Rockets | (1) Austin Prep Cougars |
| February 16, 2019 | MIAA Boys | (6) Framingham Flyers | (4) Xaverian Hawks |
| February 16, 2019 | ISL | (0) St. Mark's (Girls) | (4) BB&N (Girls) |
| February 16, 2019 | MIAA Boys | (2) Duxbury Dragons | (0) Archbishop Williams Bishops |
| February 16, 2019 | ISL | (1) St. Mark's (Boys) | (0) Lawrence Academy (Boys) |