The Boston Bruins and Montreal Canadiens share some of the most iconic moments in NHL history. It is also one of the best rivalries in hockey. For decades, Montreal dominated Boston and much of the entire league, but the Canadiens had the upper hand with 18 straight playoff series wins over the B’s over a span from 1946 to 1987.

Even though this matchup has been fairly one-sided historically, Boston has had its share of legendary moments against Montreal that are worth remembering. Some Bruins wins were hard-fought and shocked the Canadiens over the years. Let’s explore five historical victories below.

1988: Ending the losing streak

For four decades-plus, Montreal owned Boston in the playoffs. The Montreal Forum was a scary place for the Bruins, and the Boston team had many low moments there. However, Boston had an epic time in the Adams Division Final in 1988. The Bruins came into that series as a tough, balanced team coached by team legend Terry O’Reilly. Star goalie Patrick Roy led the Canadiens, who finished first in the Adams Division with 103 points and were heavy favorites entering the series.

Second-place Boston lost the first game in Montreal, but then shocked the hockey world by winning the next four games in a row. This win marked a turning point in the longtime rivalry, as the Bruins re-emerged as a top NHL team that could hand with the Canadiens competitively. Montreal’s winning streak showed that Boston had found new mental toughness after fighting off decades of frustration. The victory boosted the Bruins’ confidence over the ensuing years, as they made the first of two Stanley Cup Final appearances in three seasons.

Overall, it was a significant win for the Bruins, as they finally stopped the Canadiens’ streak of dominance and entered a new era of success.

1990: Another division win

After finally breaking through in the playoffs against the Canadiens, the Bruins got a little streak of their own going. Boston enjoyed defeating Montreal in the Adams Division Finals in 1988, then two seasons later In 1990 won the Presidents’ Trophy as the best team in the league. They were about to face an elite Canadiens defense and another round of goalie Patrick Roy.

Boston was ready to go and beat Montreal in five games. The Bruins even finished the series off at the Boston Garden for the first time since 1943. This Bruins team operated on the ice as a complete team, and its members got to tally up another playoff series win against the Canadiens.

1992: The Adams sweep

In the 1992 Adams Division Final, Boston scored its single most impressive playoff victory over Montreal. The four-game sweep was primarily due to the goaltending of Andy Moog, who quickly became known as a “Habs Killer” for his playoff performances against the Canadiens. It was the Bruins’ first sweep of their top rival since their first-ever playoff matchup in 1929. Moog bested future Hall of Famer Roy, and the offense did just enough to get the job done. Montreal couldn’t believe that they were swept, and Boston fans loved it because they were finally able to deliver some postseason misery to Canada.

2009: A franchise first

Boston had risen to the No. 1 seed in the Eastern Conference playoffs from near the bottom of the league in a few short years, and faced a clash with Montreal in the first round. The Canadiens just barely got into the playoffs that year. Even though the Bruins were the heavy favorites, the history still made things a little nerve-wracking.

These thoughts went away fast, as Boston blew through Montreal like it was preseason. The Bruins won the first two games at home and the next two on the road. The series win buried playoff anxiety, and it was the first time ever that the Bruins swept Montreal in the first round.

2011: Rallying toward the Cup

In the 2011 Eastern Conference Quarterfinals, the Canadiens were ready to continue their modern-day playoff dominance over the Bruins. Montreal went up 2-0 in the best-of-seven series, and both of those games were road wins. Boston fans were ready for another postseason collapse, but for once, the puck bounced in their favor. The Bruins bounced back and won the next two games in Montreal, including an epic overtime win in the fourth game of the series.

From there, the series went back and forth, eventually reaching a seventh game. In that do-or-die situation, the score was tied 3-3 in overtime, and Bruins forward Nathan Horton scored the game-winning goal. The victory wasn’t just another solid win against their rival; Boston went on to win the Stanley Cup that year.

This marked even more history: it was the first time ever that the Bruins had defeated the Canadiens and then gone on to win the championship in the same season. That first-round series set the tone for Boston’s playoff run and showed that they can overcome any challenging scenario. 

The above five moments showed that the Boston Bruins can overcome overwhelming odds and turn even the most one-sided rivalry into epic moments. For the Boston Bruins fan base, these memories were sweet revenge, well-earned, and are still celebrated with great admiration today.