| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (3) Natick Red Hawks at (6) Weymouth Wildcats | Connell Memorial Rink |
| December 15, 2018 | (2) Natick Red Hawks at (3) Needham Rockets | Babson Skating Center |
| December 19, 2018 | (1) Shrewsbury Colonials at (3) Natick Red Hawks | Chase Arena |
| December 22, 2018 | (1) Natick Red Hawks at (5) Lincoln-Sudbury Warriors | New England Sports Center |
| December 27, 2018 | (3) Natick Red Hawks at (3) Bridgewater-Raynham Trojans
ISLAND CREEK OYSTER CUP |
The Bog |
| December 29, 2018 | (2) Natick Red Hawks at (4) Duxbury Dragons
Island Creek Oysters Cup |
The Bog |
| January 05, 2019 | (4) Natick Red Hawks at (0) Milton Wildcats | Ulin Memorial Rink |
| January 09, 2019 | (3) Natick Red Hawks at (0) Newton North Tigers | John A. Ryan Arena |
| January 12, 2019 | (4) Framingham Flyers at (0) Natick Red Hawks | Chase Arena |
| January 16, 2019 | (2) Braintree Wamps at (3) Natick Red Hawks | Chase Arena |
| January 19, 2019 | (1) Wellesley Raiders at (3) Natick Red Hawks | Chase Arena |
| January 23, 2019 | (5) Natick Red Hawks at (2) Brookline Warriors | Walter Brown Arena |
| January 26, 2019 | (1) Weymouth Wildcats at (4) Natick Red Hawks | Chase Arena |
| January 28, 2019 | (2) Algonquin Titans at (2) Natick Red Hawks | Chase Arena |
| February 02, 2019 | (1) Newton North Tigers at (9) Natick Red Hawks | Chase Arena |
| February 06, 2019 | (4) Walpole Timberwolves at (0) Natick Red Hawks | Chase Arena |
| February 09, 2019 | (1) Natick Red Hawks at (4) Framingham Flyers | Loring Arena |
| February 13, 2019 | (1) Natick Red Hawks at (6) Wellesley Raiders | Babson Skating Center |
| February 16, 2019 | (3) Canton Bulldogs at (0) Natick Red Hawks | Chase Arena |
| February 19, 2019 | (2) Natick Red Hawks at (2) Brockton Boxers | Asiaf Skating Arena |
