The last time the Boston Bruins won the Stanley Cup was in 2011, winning the Stanley Cup in 7 games against the Presidents trophy winners, the Vancouver Canucks.
Before that they won the cup in 1972. The year Bobby Orr "Flew" in the air was 1970. The Bruins also won the Stanley Cup in 1941, 1939 and 1929, a total of 6 Stanley Cups.
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As of the 2008-09 season, that was the 1998-99 season playoffs when they defeated the Carolina Hurricanes in the Eastern Conference quarterfinals, 4 games to 2. Carolina was the 3 seed and Boston was the 6 seed.
The Boston Bruins are one of the original six teams in the National Hockey League. In the team's 90 year history they have made the playoffs seventy times not including the season that did not have playoffs because of a lockout.
I'm not certain if you mean just making the playoffs or making it all the way to the Cup Final. In any event the Bruins have been in the NHL since 1924-25. I can look up and list the years for you but why not just Google Boston Bruins for yourself and find the information you need.
The Celtics reached the second round of the 2010-2011 NBA playoffs. They were eliminated by the Miami Heat in the Eastern Conference semifinals.