| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (1) St. Peter Marian Guardians at (4) Chelmsford Lions | Hart Center |
| December 15, 2018 | (1) Chelmsford Lions at (1) Waltham Hawks | Veterans Memorial Rink |
| December 22, 2018 | (2) Chelmsford Lions at (1) Westford Academy Ghosts | Skate 3 |
| December 27, 2018 | (3) Chelmsford Lions at (0) Newton North Tigers
HILLIES CHRISTMAS TOURNAMENT |
Veterans Memorial Ice Rink |
| December 29, 2018 | (1) Chelmsford Lions at (4) Wilmington Wildcats
Hillies Hockey Christmas Tournament Championship |
Veterans Memorial Ice Rink |
| January 02, 2019 | (1) Chelmsford Lions at (0) Acton-Boxboro Revolution | Nashoba Valley Olympia |
| January 05, 2019 | (1) Central Catholic Raiders at (1) Chelmsford Lions | Chelmsford Forum |
| January 09, 2019 | (2) Chelmsford Lions at (2) Melrose Red Hawks | Kasabuski Arena |
| January 12, 2019 | (2) Billerica Indians at (1) Chelmsford Lions | Chelmsford Forum |
| January 14, 2019 | (4) Chelmsford Lions at (3) Concord-Carlisle Patriots | Edge Sports Center |
| January 16, 2019 | (1) Chelmsford Lions at (4) Andover Golden Warriors | Lawrence Valley Forum |
| January 19, 2019 | (4) Westford Academy Ghosts at (0) Chelmsford Lions | Chelmsford Forum |
| January 23, 2019 | (5) Xaverian Hawks at (0) Chelmsford Lions | Chelmsford Forum |
| January 26, 2019 | (1) Waltham Hawks at (1) Chelmsford Lions | Chelmsford Forum |
| January 30, 2019 | (0) Acton-Boxboro Revolution at (5) Chelmsford Lions | Chelmsford Forum |
| February 02, 2019 | (1) Chelmsford Lions at (0) Central Catholic Raiders | Ice Center Rink |
| February 06, 2019 | (1) Andover Golden Warriors at (3) Chelmsford Lions | Chelmsford Forum |
| February 09, 2019 | (2) Chelmsford Lions at (4) Billerica Indians | Hallenborg Memorial Pavilion |
| February 13, 2019 | (2) Danvers Falcons at (4) Chelmsford Lions | Raymond J. Bourque Arena |
| February 19, 2019 | (1) Chelmsford Lions at (4) Medford Mustangs
Cahoon Cup |
Burlington Ice Palace |
| February 21, 2019 | (4) Burlington Red Devils at (0) Chelmsford Lions
CAHOON CUP CONSOLATION |
Burlington Ice Palace |
| February 28, 2019 | (2) Chelmsford Lions at (4) Billerica Indians | Chelmsford Forum |
