| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (0) East Boston Jets at (8) Dover-Sherborn/Weston Raiders | Chase Arena |
| December 21, 2019 | (9) Greater Lowell/Nashoba Tech Vikings at (1) East Boston Jets | Lt. Porrazzo Memorial Rink |
| December 26, 2019 | (8) Ashland Clockers at (0) East Boston Jets
East Boston DEEP FREEZE TOURNAMENT |
Lt. Porrazzo Memorial Rink |
| December 27, 2019 | (7) OBryant Tigers at (2) East Boston Jets
EAST BOSTON DEEP FREEZE TOURNAMENT |
Lt. Porrazzo Memorial Rink |
| December 30, 2019 | (0) East Boston Jets at (1) Holliston Panthers | Loring Arena |
| January 07, 2020 | (0) East Boston Jets at (1) Latin Academy Dragons | Matthews Arena |
| January 08, 2020 | (0) East Boston Jets at (1) Revere/Malden Patriots
East Boston Forfeit |
Cronin Skating Rink |
| January 11, 2020 | (0) East Boston Jets at (1) Minuteman Mustangs
East Boston forfeit |
Valley Sports Arena |
| January 18, 2020 | (11) Minuteman Mustangs at (0) East Boston Jets | Lt. Porrazzo Memorial Rink |
| January 21, 2020 | (7) Latin Academy Dragons at (0) East Boston Jets | Lt. Porrazzo Memorial Rink |
| January 30, 2020 | (0) East Boston Jets at (8) OBryant Tigers | Matthews Arena |
| February 01, 2020 | (8) Rockport Vikings at (1) East Boston Jets | Lt. Porrazzo Memorial Rink |
| February 05, 2020 | (0) East Boston Jets at (1) Rockport Vikings
East Boston Forfeit |
Dorothy Talbot Rink |
| February 08, 2020 | (0) East Boston Jets at (12) Greater Lowell/Nashoba Tech Vikings | Chelmsford Forum |
| February 15, 2020 | (11) Revere/Malden Patriots at (0) East Boston Jets | Lt. Porrazzo Memorial Rink |
