Playoff Meetings: 33 times (Canadiens lead 24-8, one ongoing)
It’s tough not to build a rivalry when you’ve met more times in both the regular season and playoffs than any other two teams in your sport. The current playoff series between Boston and Montreal is their 33rd postseason battle, 10 more than any other NHL pairing. The Canadiens have historically dominated the playoff meetings, having won 24 series to Boston’s eight.
Those early days managed to boil the bad blood and create great moments to last until today. And one was more memorable than Game 7 of the 1952 Stanley Cup semifinals when Maurice 'Rocket' Richard was bloodied and concussed, but came back wearing a bandage to score the series-winning goal for Montreal.
From 1965 to 1979, the Canadiens or Bruins won 12 of 15 Stanley Cups (to be fair, the Canadiens won 10 of them) and were consistently two of the top teams in the league, but the Habs still owned the Bruins in the playoffs, winning every series between the two powerhouses in the '60s and '70s.
Since 1984, the Canadiens only hold an 8-6 advantage over the Bruins in the playoffs, and from 1984-1992 they met every postseason. Of their 32 series completed to date, nine have gone the maximum number of games.