The Boston Bruins made their second appearance in the Winter Classic, as they played against the Philadelphia Flyers in the 2010 NHL Winter Classic held in Boston's Fenway Park; Massachusetts became the first market to serve as repeat host of the Winter Classic. This was the first Winter Classic appearance and third outdoor game for the Montreal Canadiens; the team previously played 2003 NHL Heritage Classic against the hosting Edmonton Oilers and the 2011 NHL Heritage Classic against the hosting Calgary Flames.
Besides the official NHL Winter Classic Spectator Plaza pre-game activites included tailgaiting in the parking lots, a walk through Patriot Place and Gillette Stadium.
The Boston Bruins and Montreal Canadiens enter the rink for the official pre-game warm-up at Gillette Stadium.
In the most lopsided score in the Winter Classic, four Montreal players combined to score five goals en route to a 5–1 victory against Boston. In his first game since suffering a hand injury on November 22, Canadiens forward Brendan Gallagher recorded a goal and an assist. Goalie Mike Condon made 27 saves for Montreal. Matt Beleskey scored the Bruins' only goal.