No matter the outcome, it's slated to be a special event, as nearly 70,000 fans will witness another chapter in this heated battle. On the ice, it's an important game for both teams as far as the standings are concerned.
Here's what to watch for:
The Canadiens are one point ahead of the Bruins in the Atlantic Division standings and both teams have been struggling. Montreal captain Max Pacioretty believes a victory could jump-start a winning streak for the Canadiens.
"It could change a lot," he said after the team's practice Thursday. "Everyone's seen our division and how tight it is. Every night we're looking at scores and you can go from first place to out of a playoff spot almost with two points. First and foremost, we have to concentrate on two points.
"If we can pull out a good game [Friday] and get the victory, it could be a good jump start for things to come."
The Bruins have been inconsistent this season, but snapped a three-game losing skid in dramatic fashion against the Ottawa Senators on Tuesday. Boston believes it can build on that victory in the Winter Classic.
The Canadiens are getting a massive addition to their lineup with forward Brendan Gallagher returning. He missed the past five weeks due to a broken hand and was given medical clearance on Thursday. He said he's 100 percent healthy and wouldn't play if he wasn't. Pacioretty is thrilled to have his linemate back.
"I enjoy playing with Gally a lot because we've had a lot of good success in the past, but he's easy to play with and you always know what he's going to do with the puck," the captain said. "It's a simple game going out there with him. He's going to do the dirty work and makes it a lot easier on his linemates. We've had that chemistry for a couple of years now and hopefully we can pick up right where we left off."
The line of Pacioretty, Gallagher and Tomas Plekanec will be reunited.
While the Canadiens get Gallagher back, the Bruins will be without the services of forward Brad Marchand, who was suspended for three games for his hit on Ottawa's Mark Borowiecki. It also doesn't help that the Bruins are already without top-line center David Krejci, who is week-to-week with an upper-body injury.
"I know Brad's a big part of their team, so I'm sure they're going to miss him," said Montreal's P.K. Subban.
As a result of Marchand's suspension, the Bruins recalled forward Alex Khokhlachev from Providence of the AHL and assigned defenseman Colin Miller to the P-Bruins.
For any outdoor game, ice conditions are always a concern. The league does a tremendous job of getting the ice in good shape for the Winter Classic. After practicing on Thursday, players on both teams mentioned the soft and slushy conditions. The sun made one end of the ice a little choppy, but players were hoping it would be better for game time.
When the Bruins played in the 2010 Winter Classic against the Philadelphia Flyers at Fenway Park, Boston goaltender Tuukka Rask served as the backup to Tim Thomas. Rask will get the start on Friday and will be sporting an impressive new mask that pays homage to the Patriots and the old Boston Garden. Rask has a 4-14-3 record against the Canadiens in his career.
At the other end of the ice, rookie netminder and Boston native Mike Condon will get the start. He's 1-1-0 against the Bruins this season. Like Rask, Condon also honors the Patriots with a photo of coach Bill Belichick on the back of his mask.