As they prepare for the ninth such meeting on Wednesday night (CBC, CBCSports.ca, 6:30 p.m.), here's a look at their most memorable series deciders.
1952: Rocket's red glare
Setup: Boston led the semifinal series 3-2 but the Canadiens tied the series in Massachusetts with key contributions from Paul Masnick and Eddie Mazur, who became one of the first NHL players ever to score a playoff goal before his first regular-season goal.
Game 7 hero: Maurice Richard. No quiet room here. The Rocket allegedly was knocked out for 15 seconds after a hit from Leo Labine, but he came back to snap a tie in a 3-1 win.
Quote: "Please, no handshakes. There are six stitches in my head and it hurts," Richard told reporters after.
What happened next: The Canadiens were no match for Detroit in the final, swept in four. That continued the longest championship drought for the Habs in the post-war Original Six era, a whopping six years. They beat the Bruins in the Cup final the following season.
1971: Cool young customer
Setup: The Bruins had a 24-point regular-season advantage with Bobby Orr and Phil Esposito at the height of their powers. Boston appeared headed to a two-game cushion with a 5-1 lead in Game 2 before a stunning comeback led by Jean Beliveau.
Game 7 hero: Montreal coach Al MacNeil bypassed regular-season netminders Rogie Vachon and Phil Myre in favour of six-game rookie Ken Dryden. The former Bruins draft pick stood tall in a 4-2 win in the clincher, and faced an average of 41 shots per game in the series.
Quote: "Maybe I appear very cool, but the pressure is there and I feel it," the future Hall of Famer said.
What happened next: The Habs overcame some early struggles against Minnesota and then rallied from 2-0 and 3-2 deficits against Chicago in the final, the last series for Beliveau.
1979: Penalty for the ages
Setup: The home team won every game of the series, leading to the legendary final game at the Forum, which the Bruins led 3-1. Boston coach Don Cherry and his crew had an infamous miscommunication, resulting in a late third period too-many-men penalty and Montreal's third power-play goal, a Guy Lafleur howitzer that sent the game to overtime. Yvon Lambert won it for the Habs in the extra frame.
Game 7 hero: Bruins goalie Gilles Gilbert, a Quebec native, was universally hailed as the game's first star despite the result. Habs sniper Steve Shutt likened the experience to "shooting at a brick wall."
Quote: "I grabbed two other guys trying to go over the boards," Cherry told the Globe and Mail's Scott Young after the game. "That would have made eight on the ice. Might as well have let them go."
What happened next: In many ways, the Bruins-Canadiens series felt like the Stanley Cup final. After an emotional letdown in the first game of the final against the New York Rangers, the Habs fairly breezed in the next four, hoisting the Cup on Forum ice for the first time since 1968.
1994: Rough justice for Roy
Setup: Future Hall of Famer Patrick Roy was more than game in the conference quarter-finals, dealing with appendicitis while giving the Habs a 3-2 lead as they aimed to repeat as Stanley Cup champions. But Boston would prevail in Game 6, the last ever played at the legendary Forum.
Game 7 hero: Really, it was total team effort for Boston, who won despite missing 50-goal scorer Cam Neely. Boston roared to a 4-0 lead after 25 minutes (Fred Knipscheer goal, anyone?) but after the Habs came to life, it was left to Bruins great Ray Bourque to seal the deal with their final goal in a 5-3 victory.
Quote: "It was just justice that was made," Montreal coach Jacques Demers said. "They should have won the series long ago. We were fortunate to be here for Game 7."
What happened next: This was a matchup of two mid-range Eastern teams, and reflecting that, Boston was eliminated in the next round by rookie goalie Martin Brodeur and the New Jersey Devils.
2004: Theodore a pain for Thornton, Bruins
Setup: Boston was considered the favourite after an 11-point edge in the regular season, and they played like it early on, building 2-0 and 3-1 leads. But the Bruins would implode in what was the turning point with the team for Joe Thornton. The former No. 1 overall pick and team captain battled through a rib injury and was perhaps unwise to suit up at all, going pointless in seven games.
Game 7 hero: Richard Zednik broke a scoreless tie with nine minutes left, but it was goalie Jose Theodore who stole a game for at least the second time in the series, with a shutout in the 2-0 finale.
Quote: "Teams are successful because of goaltending in this league. He was at his best when it really counted," said Canadiens coach Claude Julien.
What happened next: The good vibes lasted about three days as the Habs were swept in the next round by eventual Stanley Cup champion Tampa Bay.
2011: Horton to the rescue
Setup: Boston fans were ready to groan again after the No. 6-seeded Habs came into Boston and outscored the home team 5-1 while winning the first two games. But in a reversal of the historical overtime trend in the rivalry, Boston would go on to win three series games in overtime.
Game 7 hero: Nathan Horton, who notched the double-OT winner in Game 5, came through again with a shot to the Montreal net that eluded P.K. Subban, Hal Gill and Price just under six minutes into overtime.
Quote: "For us, it's nice to reward our fans with this because they've been punished enough [against Montreal]," said Julien, now coaching the Bruins.
What happened next: The Bruins went on to play Game 7 twice more that spring, a nailbiter win against Tampa Bay and a comfortable victory in pre-riot Vancouver, ending a 39-year Stanley Cup drought.
Boston rode Andy Moog's stellar netminding to a 1991 quarter-final victory, while Carey Price rebounded from two bad outings to post a Game 7 shutout in a 2008 first-round series.
Both the '91 Bruins and '08 Canadiens were eliminated in their next series.