| Date & Time | Game | Venue |
|---|---|---|
| December 16, 2019 | (7) Tewksbury Redmen at (1) Chelmsford Lions | Chelmsford Forum |
| December 22, 2019 | (2) Tewksbury Redmen at (5) North Andover Scarlet Knights | Merrimack College |
| December 26, 2019 | (5) Tewksbury Redmen at (0) Biddeford (Maine) | USM Ice Arena |
| December 27, 2019 | (4) Tewksbury Redmen at (0) Scarborough (Maine) | USM Ice Arena |
| December 28, 2019 | (6) Tewksbury Redmen at (1) Thornton Academy (Maine)
Yankee Ford Holiday Classic |
USM Ice Arena |
| January 02, 2020 | (5) Tewksbury Redmen at (2) Dracut/Tyngsboro Middies | Ice Center Rink |
| January 04, 2020 | (4) Boston Latin Wolfpack at (1) Tewksbury Redmen | Breakaway Ice Center |
| January 08, 2020 | (2) Lincoln-Sudbury Warriors at (4) Tewksbury Redmen | Breakaway Ice Center |
| January 12, 2020 | (3) Tewksbury Redmen at (0) Lowell Red Raiders | Tsongas Center |
| January 13, 2020 | (1) Westford Academy Ghosts at (4) Tewksbury Redmen | Breakaway Ice Center |
| January 15, 2020 | (5) Tewksbury Redmen at (2) Concord-Carlisle Patriots | Edge Sports Center |
| January 18, 2020 | (6) Tewksbury Redmen at (1) Haverhill Hillies | Veterans Memorial Ice Rink |
| January 20, 2020 | (1) Billerica Indians at (7) Tewksbury Redmen | Breakaway Ice Center |
| January 29, 2020 | (2) North Andover Scarlet Knights at (2) Tewksbury Redmen | Breakaway Ice Center |
| February 01, 2020 | (1) Concord-Carlisle Patriots at (3) Tewksbury Redmen | Breakaway Ice Center |
| February 05, 2020 | (5) Tewksbury Redmen at (5) Boston Latin Wolfpack | Murphy Memorial Rink |
| February 08, 2020 | (1) Tewksbury Redmen at (5) Lincoln-Sudbury Warriors | New England Sports Center |
| February 10, 2020 | (3) Tewksbury Redmen at (4) BC High Eagles | Clark Athletic Center |
| February 12, 2020 | (4) Lowell Red Raiders at (4) Tewksbury Redmen | Breakaway Ice Center |
| February 19, 2020 | (0) Haverhill Hillies at (5) Tewksbury Redmen | Breakaway Ice Center |
| February 20, 2020 | (2) Wilmington Wildcats at (3) Tewksbury Redmen
Rivalry Game |
Breakaway Ice Center |
| February 25, 2020 | (0) North Reading Hornets at (4) Tewksbury Redmen
BOYS D2 N Playoff |
Chelmsford Forum |
| February 28, 2020 | (3) North Andover Scarlet Knights at (2) Tewksbury Redmen
Boys D2 N Playoff |
Chelmsford Forum |
