| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (3) Medfield Warriors at (1) Burrillville (R.I.) | Levy Ice Rink |
| December 15, 2018 | (3) Holliston Panthers at (3) Medfield Warriors | Pirelli Veterans Arena |
| December 20, 2018 | (3) Hopkinton Hillers at (6) Medfield Warriors | Pirelli Veterans Arena |
| December 22, 2018 | (2) Medfield Warriors at (1) Norton Lancers | Foxboro Sports Center |
| January 05, 2019 | (3) Medfield Warriors at (2) Ashland Clockers | Loring Arena |
| January 09, 2019 | (4) Medfield Warriors at (0) Dedham Marauders | Noble & Greenough School |
| January 12, 2019 | (1) Westwood Wolverines at (1) Medfield Warriors | Pirelli Veterans Arena |
| January 16, 2019 | (1) Medfield Warriors at (1) Medway Mustangs | Pirelli Veterans Arena |
| January 19, 2019 | (2) Medfield Warriors at (2) Norwood Mustangs | Rodman Arena |
| January 21, 2019 | (6) Medfield Warriors at (2) Bishop Feehan Shamrocks | New England Sports Village |
| January 23, 2019 | (1) Bellingham Blackhawks at (4) Medfield Warriors | Pirelli Veterans Arena |
| January 26, 2019 | (5) Medfield Warriors at (1) Holliston Panthers | Blackstone Valley Ice Arena |
| January 30, 2019 | (2) Medfield Warriors at (1) Hopkinton Hillers | Navin Arena |
| February 02, 2019 | (4) Medfield Warriors at (5) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 07, 2019 | (0) Ashland Clockers at (2) Medfield Warriors | Pirelli Veterans Arena |
| February 09, 2019 | (2) Dover-Sherborn/Weston Raiders at (4) Medfield Warriors | Pirelli Veterans Arena |
| February 13, 2019 | (1) Medfield Warriors at (3) Westwood Wolverines | Canton Ice House |
| February 16, 2019 | (1) Norwood Mustangs at (1) Medfield Warriors | Pirelli Veterans Arena |
| February 19, 2019 | (2) Medfield Warriors at (4) Coyle & Cassidy Warriors
JOE Quinn Memorial Tournament |
Raynham IcePlex |
| February 21, 2019 | (0) Medfield Warriors at (4) Boston Latin Wolfpack
joe Quinn Memorial Tournament Consolation |
Raynham IcePlex |
| February 26, 2019 | (0) Nauset Warriors at (3) Medfield Warriors | Gallo Arena |
| March 02, 2019 | (4) Medfield Warriors at (0) Southeastern/Bristol-Plymouth Hawks | Gallo Arena |
| March 05, 2019 | (3) Westwood Wolverines at (2) Medfield Warriors | Gallo Arena |
