| Date & Time | Game | Venue |
|---|---|---|
| December 13, 2017 | (2) Lincoln-Sudbury Warriors at (6) Winchester Red & Black | O'Brien Arena |
| December 16, 2017 | (8) Winchester Red & Black at (0) Wakefield Warriors | Stoneham Arena |
| December 19, 2017 | (5) Natick Red Hawks at (4) Winchester Red & Black | O'Brien Arena |
| December 23, 2017 | (1) Winchester Red & Black at (2) Burlington Red Devils | Burlington Ice Palace |
| December 27, 2017 | (1) Newburyport Clippers at (0) Winchester Red & Black | O'Brien Arena |
| December 30, 2017 | (3) St. Mary's Lynn Spartans at (1) Winchester Red & Black | O'Brien Arena |
| January 03, 2018 | (9) Winchester Red & Black at (0) Lexington Minutemen | Edge Sports Center |
| January 06, 2018 | (2) Reading Rockets at (3) Winchester Red & Black | O'Brien Arena |
| January 10, 2018 | (4) Belmont Marauders at (3) Winchester Red & Black | O'Brien Arena |
| January 13, 2018 | (2) Winchester Red & Black at (3) Arlington Spy Ponders | Ed Burns Arena |
| January 15, 2018 | (0) Xaverian Hawks at (3) Winchester Red & Black
Middlesex League-Catholic Conference Challenge |
O'Brien Arena |
| January 20, 2018 | (4) Winchester Red & Black at (2) Woburn Tanners | O'Brien Arena |
| January 23, 2018 | (2) Wilmington Wildcats at (7) Winchester Red & Black | O'Brien Arena |
| January 27, 2018 | (2) Winchester Red & Black at (2) Stoneham Spartans | Stoneham Arena |
| January 30, 2018 | (3) Melrose Red Hawks at (2) Winchester Red & Black | O'Brien Arena |
| February 03, 2018 | (0) Lexington Minutemen at (3) Winchester Red & Black | O'Brien Arena |
| February 08, 2018 | (3) Winchester Red & Black at (2) Reading Rockets
rescheduled from February 7th |
Burbank Ice Arena |
| February 10, 2018 | (3) Winchester Red & Black at (0) Belmont Marauders | Skip Viglirolo Rink |
| February 14, 2018 | (3) Arlington Spy Ponders at (3) Winchester Red & Black | O'Brien Arena |
| February 17, 2018 | (0) Woburn Tanners at (1) Winchester Red & Black | O'Brien Arena |
| February 19, 2018 | (4) Winchester Red & Black at (0) Bishop Feehan Shamrocks | New England Sports Village |
| February 28, 2018 | (1) Reading Rockets at (5) Winchester Red & Black | Chelmsford Forum |
| March 03, 2018 | (3) Winchester Red & Black at (2) St. Mary's Lynn Spartans | O'Brien Arena |
| March 08, 2018 | (0) Newburyport Clippers at (1) Winchester Red & Black
Div I North Semi-Finals |
Tsongas Center |
| March 14, 2018 | (0) Winchester Red & Black at (6) Waltham Hawks
Div I North Finals |
Tsongas Center |
