| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2018 | (5) Hingham Harbormen at (2) St. John's Prep Eagles | Essex Sports Center |
| December 19, 2018 | (0) Andover Golden Warriors at (2) St. John's Prep Eagles | Essex Sports Center |
| December 22, 2018 | (0) Framingham Flyers at (6) St. John's Prep Eagles | Essex Sports Center |
| December 27, 2018 | (1) BC High Eagles at (1) St. John's Prep Eagles | Essex Sports Center |
| December 28, 2018 | (3) St. John's Prep Eagles at (3) Central Catholic Raiders
Pete Frates Winter Classic Consolation Game |
Essex Sports Center |
| January 02, 2019 | (1) St. John's Prep Eagles at (2) Reading Rockets | Burbank Ice Arena |
| January 05, 2019 | (1) Malden Catholic Lancers at (7) St. John's Prep Eagles | Essex Sports Center |
| January 09, 2019 | (1) St. John's Prep Eagles at (2) BC High Eagles | Clark Athletic Center |
| January 12, 2019 | (4) Xaverian Hawks at (3) St. John's Prep Eagles | Essex Sports Center |
| January 16, 2019 | (1) St. John's Prep Eagles at (3) Austin Prep Cougars | Stoneham Arena |
| January 21, 2019 | (3) St. John's Prep Eagles at (3) Melrose Red Hawks | O'Brien Arena |
| January 23, 2019 | (2) St. John's Prep Eagles at (1) Malden Catholic Lancers | Valley Forum II |
| January 30, 2019 | (0) St. John's Prep Eagles at (5) Xaverian Hawks | Canton Ice House |
| February 02, 2019 | (2) Newburyport Clippers at (5) St. John's Prep Eagles | Essex Sports Center |
| February 06, 2019 | (3) Mount St. Charles (R.I.) at (5) St. John's Prep Eagles | Essex Sports Center |
| February 09, 2019 | (5) St. John's Prep Eagles at (2) Saint John's Shrewsbury Pioneers | New England Sports Center |
| February 13, 2019 | (0) St. John's Prep Eagles at (3) Catholic Memorial Knights | Warrior Ice Arena |
| February 18, 2019 | (0) Catholic Memorial Knights at (2) St. John's Prep Eagles
new date per paul mac |
Essex Sports Center |
| February 20, 2019 | (4) St. John's Prep Eagles at (1) Needham Rockets | Babson Skating Center |
| February 22, 2019 | (2) Danvers Falcons at (4) St. John's Prep Eagles | Essex Sports Center |
| February 28, 2019 | (7) St. John's Prep Eagles at (0) Westford Academy Ghosts | O'Brien Arena |
| March 03, 2019 | (3) St. John's Prep Eagles at (2) St. Mary's Lynn Spartans | Chelmsford Forum |
| March 07, 2019 | (2) Andover Golden Warriors at (4) St. John's Prep Eagles | Tsongas Center |
| March 11, 2019 | (4) Winchester Red & Black at (1) St. John's Prep Eagles | Tsongas Center |
