| Date & Time | Game | Venue |
|---|---|---|
| December 12, 2019 | (1) Westboro Rangers at (2) Marlboro Panthers | NorthStar Ice Sports |
| December 14, 2019 | (2) Westboro Rangers at (1) Algonquin Titans
Borough's Cup |
NorthStar Ice Sports |
| December 18, 2019 | (5) Hudson Hawks at (3) Westboro Rangers | NorthStar Ice Sports |
| December 21, 2019 | (1) Westboro Rangers at (4) North Middlesex Patriots | Wallace Civic Center |
| December 23, 2019 | (2) Westboro Rangers at (7) Haverhill Hillies | Veterans Memorial Ice Rink |
| December 27, 2019 | (3) Essex Tech Hawks at (2) Westboro Rangers
Hillies Christmas Tournament |
Veterans Memorial Ice Rink |
| December 28, 2019 | (0) Westboro Rangers at (3) Auburn/Millbury Rockets | Horgan Skating Arena |
| January 08, 2020 | (2) Auburn/Millbury Rockets at (4) Westboro Rangers | NorthStar Ice Sports |
| January 11, 2020 | (1) East Longmeadow Spartans at (1) Westboro Rangers | NorthStar Ice Sports |
| January 15, 2020 | (2) Nashoba Wolves at (5) Westboro Rangers | NorthStar Ice Sports |
| January 20, 2020 | (1) Westboro Rangers at (3) Grafton Gators | Buffone Arena |
| January 22, 2020 | (5) Leominster Blue Devils at (4) Westboro Rangers | NorthStar Ice Sports |
| January 25, 2020 | (5) Wachusett Mountaineers at (3) Westboro Rangers | NorthStar Ice Sports |
| January 29, 2020 | (1) Westboro Rangers at (4) Groton-Dunstable Crusaders | Groton School Rink |
| February 01, 2020 | (2) Westboro Rangers at (6) Northbridge Rams | New England Sports Center |
| February 05, 2020 | (2) Westboro Rangers at (8) Hudson Hawks | New England Sports Center |
| February 08, 2020 | (2) St. Peter Marian Guardians at (5) Westboro Rangers | NorthStar Ice Sports |
| February 12, 2020 | (1) Westboro Rangers at (2) Algonquin Titans | NorthStar Ice Sports |
| February 17, 2020 | (1) Westboro Rangers at (4) Westfield Bombers | Amelia Park Rink |
| February 17, 2020 | (1) Westboro Rangers at (4) Westfield Bombers
pp from 01/18/2020 |
Amelia Park Rink |
| February 19, 2020 | (0) Westboro Rangers at (4) Marlboro Panthers | Navin Arena |
