| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2018 | (3) Westboro Rangers at (2) Wachusett Mountaineers
Bourough's Cup |
NorthStar Ice Sports |
| December 15, 2018 | (3) Algonquin Titans at (2) Westboro Rangers | NorthStar Ice Sports |
| December 17, 2018 | (4) Westboro Rangers at (2) Leominster Blue Devils | Wallace Civic Center |
| December 19, 2018 | (3) Westboro Rangers at (0) Groton-Dunstable Crusaders | Pratt School Rink |
| December 22, 2018 | (2) Wayland Warriors at (4) Westboro Rangers | NorthStar Ice Sports |
| December 26, 2018 | (1) Westboro Rangers at (3) North Middlesex Patriots | Wallace Civic Center |
| December 29, 2018 | (2) Westboro Rangers at (0) Auburn/Millbury Rockets | Horgan Skating Arena |
| January 02, 2019 | (2) Hudson Hawks at (0) Westboro Rangers | NorthStar Ice Sports |
| January 09, 2019 | (2) Holliston Panthers at (4) Westboro Rangers | NorthStar Ice Sports |
| January 12, 2019 | (3) Westboro Rangers at (1) Marlboro Panthers | Navin Arena |
| January 21, 2019 | (5) Westboro Rangers at (1) Hudson Hawks | New England Sports Center |
| January 23, 2019 | (4) Grafton Gators at (3) Westboro Rangers | NorthStar Ice Sports |
| January 26, 2019 | (3) Marlboro Panthers at (0) Westboro Rangers | NorthStar Ice Sports |
| February 06, 2019 | (1) Nashoba Wolves at (5) Westboro Rangers | NorthStar Ice Sports |
| February 09, 2019 | (3) Westboro Rangers at (5) Acton-Boxboro Revolution | Nashoba Valley Olympia |
| February 13, 2019 | (3) Auburn/Millbury Rockets at (5) Westboro Rangers | NorthStar Ice Sports |
| February 16, 2019 | (4) Algonquin Titans at (0) Westboro Rangers | NorthStar Ice Sports |
| February 18, 2019 | (5) Westboro Rangers at (1) Nashoba Wolves | New England Sports Center |
| February 20, 2019 | (2) Westfield Bombers at (0) Westboro Rangers | NorthStar Ice Sports |
| February 22, 2019 | (0) Leominster Blue Devils at (4) Westboro Rangers | NorthStar Ice Sports |
| March 02, 2019 | (3) Groton-Dunstable Crusaders at (0) Westboro Rangers | NorthStar Ice Sports |
