| Date & Time | Game | Venue |
|---|---|---|
| December 21, 2019 | (1) St. John's Prep Eagles at (9) Hingham Harbormen | Pilgrim Arena |
| December 23, 2019 | (3) St. John's Prep Eagles at (1) Danvers Falcons | Raymond J. Bourque Arena |
| December 27, 2019 | (1) BC High Eagles at (1) St. John's Prep Eagles | Essex Sports Center |
| December 28, 2019 | (1) Pope Francis Cardinals at (2) St. John's Prep Eagles
Pete Frates Tournament Consolation Game |
Essex Sports Center |
| January 01, 2020 | (0) Xaverian Hawks at (3) St. John's Prep Eagles | Essex Sports Center |
| January 04, 2020 | (0) St. John's Prep Eagles at (2) Catholic Memorial Knights | Babson Skating Center |
| January 08, 2020 | (1) St. John's Prep Eagles at (0) Framingham Flyers | Loring Arena |
| January 11, 2020 | (2) St. John's Prep Eagles at (2) Malden Catholic Lancers | Valley Forum II |
| January 14, 2020 | (2) St. John's Prep Eagles at (4) BC High Eagles | Clark Athletic Center |
| January 18, 2020 | (5) St. John's Prep Eagles at (1) Xaverian Hawks | Canton Ice House |
| January 20, 2020 | (1) Reading Rockets at (1) St. John's Prep Eagles | Essex Sports Center |
| January 22, 2020 | (1) Catholic Memorial Knights at (1) St. John's Prep Eagles | Essex Sports Center |
| January 25, 2020 | (2) Austin Prep Cougars at (6) St. John's Prep Eagles | Essex Sports Center |
| January 29, 2020 | (1) Malden Catholic Lancers at (2) St. John's Prep Eagles | Essex Sports Center |
| February 01, 2020 | (2) Saint John's Shrewsbury Pioneers at (1) St. John's Prep Eagles | Essex Sports Center |
| February 05, 2020 | (4) St. John's Prep Eagles at (4) Andover Golden Warriors | Lawrence Valley Forum |
| February 08, 2020 | (2) Newburyport Clippers at (10) St. John's Prep Eagles
12th Hines Memorial |
Essex Sports Center |
| February 12, 2020 | (1) Mount St. Charles (R.I.) at (4) St. John's Prep Eagles | Essex Sports Center |
| February 15, 2020 | (9) St. John's Prep Eagles at (2) Billerica Indians | Hallenborg Memorial Pavilion |
| February 19, 2020 | (1) Needham Rockets at (9) St. John's Prep Eagles | Essex Sports Center |
| February 26, 2020 | (1) Xaverian Hawks at (2) St. John's Prep Eagles
Boys Division 1A: Game 2 |
Loring Arena |
| March 01, 2020 | (1) St. John's Prep Eagles at (3) Arlington Spy Ponders
Super 8 |
Stoneham Arena |
| March 04, 2020 | (2) Catholic Memorial Knights at (5) St. John's Prep Eagles
Super 8 quarter final |
Stoneham Arena |
| March 07, 2020 | (3) St. John's Prep Eagles at (2) BC High Eagles
Boys Division 1A: Game 12 |
Loring Arena |
| March 11, 2020 | (2) St. John's Prep Eagles at (3) Pope Francis Cardinals
Boys Division 1A: Game 13 |
Loring Arena |
