| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (1) Needham Rockets at (1) Natick Red Hawks | Chase Arena |
| December 21, 2019 | (2) Algonquin Titans at (4) Natick Red Hawks | Chase Arena |
| December 23, 2019 | (3) Concord-Carlisle Patriots at (4) Natick Red Hawks | Chase Arena |
| December 27, 2019 | (3) Natick Red Hawks at (2) Barnstable Red Hawks | The Bog |
| December 28, 2019 | (3) Natick Red Hawks at (3) Duxbury Dragons
Island Creek Oysters Cup Championship Game |
The Bog |
| January 01, 2020 | (2) Natick Red Hawks at (3) Wachusett Mountaineers | NorthStar Ice Sports |
| January 04, 2020 | (2) Milton Wildcats at (2) Natick Red Hawks | Chase Arena |
| January 08, 2020 | (1) Newton North Tigers at (4) Natick Red Hawks | Chase Arena |
| January 11, 2020 | (2) Natick Red Hawks at (3) Framingham Flyers | Loring Arena |
| January 15, 2020 | (2) Natick Red Hawks at (1) Braintree Wamps | Zapustas Arena |
| January 18, 2020 | (1) Natick Red Hawks at (0) Wellesley Raiders | Wellesley Sports Center |
| January 22, 2020 | (2) Brookline Warriors at (3) Natick Red Hawks | Chase Arena |
| January 25, 2020 | (1) Natick Red Hawks at (0) Weymouth Wildcats | Connell Memorial Rink |
| January 29, 2020 | (2) Natick Red Hawks at (1) Shrewsbury Colonials | NorthStar Ice Sports |
| February 01, 2020 | (4) Natick Red Hawks at (0) Newton North Tigers | John A. Ryan Arena |
| February 05, 2020 | (2) Natick Red Hawks at (1) Walpole Timberwolves | Rodman Arena |
| February 08, 2020 | (0) Framingham Flyers at (1) Natick Red Hawks | Chase Arena |
| February 12, 2020 | (2) Wellesley Raiders at (2) Natick Red Hawks | Chase Arena |
| February 15, 2020 | (1) Wayland Warriors at (10) Natick Red Hawks | Chase Arena |
| February 19, 2020 | (1) Lincoln-Sudbury Warriors at (1) Natick Red Hawks | Chase Arena |
| February 26, 2020 | (2) Milton Wildcats at (4) Natick Red Hawks
Boys D1 S Playoff |
John A. Ryan Arena |
| February 29, 2020 | (3) Franklin Panthers at (1) Natick Red Hawks
Boys D1 S Playoff |
Loring Arena |
