| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2018 | (3) Needham Rockets at (0) Natick Red Hawks | Chase Arena |
| December 19, 2018 | (6) Natick Red Hawks at (1) Brookline Warriors | Walter Brown Arena |
| December 22, 2018 | (3) Natick Red Hawks at (3) Shrewsbury Colonials | NorthStar Ice Sports |
| December 26, 2018 | (5) Notre Dame Academy (Hingham) Cougars at (4) Natick Red Hawks | Chase Arena |
| December 29, 2018 | (2) Algonquin/Hudson Titans at (1) Natick Red Hawks | Chase Arena |
| January 05, 2019 | (2) Milton Wildcats at (10) Natick Red Hawks | Chase Arena |
| January 09, 2019 | (2) Newton North/South Tigers at (2) Natick Red Hawks | Chase Arena |
| January 12, 2019 | (6) Natick Red Hawks at (1) Framingham Flyers | Loring Arena |
| January 16, 2019 | (0) Natick Red Hawks at (1) Braintree Wamps | Zapustas Arena |
| January 18, 2019 | (1) Natick Red Hawks at (4) Needham Rockets | Lane Rink (St. Sebs) |
| January 19, 2019 | (1) Natick Red Hawks at (3) Wellesley Raiders | Babson Skating Center |
| January 21, 2019 | (7) Natick Red Hawks at (1) Archbishop Williams Bishops | Zapustas Arena |
| January 23, 2019 | (0) Brookline Warriors at (3) Natick Red Hawks | Chase Arena |
| January 26, 2019 | (6) Natick Red Hawks at (1) Weymouth Wildcats | Connell Memorial Rink |
| January 30, 2019 | (5) Natick Red Hawks at (5) Algonquin/Hudson Titans | New England Sports Center |
| February 02, 2019 | (4) Natick Red Hawks at (1) Newton North/South Tigers | John A. Ryan Arena |
| February 06, 2019 | (1) Natick Red Hawks at (2) Walpole Timberwolves | Rodman Arena |
| February 09, 2019 | (1) Framingham Flyers at (4) Natick Red Hawks | Chase Arena |
| February 13, 2019 | (4) Wellesley Raiders at (0) Natick Red Hawks | Chase Arena |
| February 18, 2019 | (5) Natick Red Hawks at (3) Medway/Ashland Mustangs
makeup game FROM 2-12 |
Pirelli Veterans Arena |
| February 25, 2019 | (3) Natick Red Hawks at (1) Stoneham Spartans | Stoneham Arena |
| March 02, 2019 | (1) Natick Red Hawks at (6) Westwood Wolverines | Canton Ice House |
