I have seen 3 Bruins Cups in my lifetime and there should have been a few more but......
1971 - Bobby Orr did not play well in Game 2 against Montreal in the first round and it cost them.
1974 - They underestimated the Flyers who had not won in Boston since 1967
They made the SCF in 1977 and 1978 but they were not going to beat Montreal
1979 - TOO MANY MEN
Returned to the SCF in 1988 and 1990 - 88 they had no chance, 90 they never recovered from losing Game 1 in 3 OTs.
The team had trouble adjusting to the replacement of the Boston Garden and then was left in shambles after the lost 2004-05 season. Jacobs 'retired' Harry Sinden and after a disastrous year with Dave Lewis as coach struck gold with Claude Julien in 2007-08.
The Bruins stumbled in 2012 against Washington and once again Montreal got in their heads in 2014. People overlook that in 2013 the Bruins with a couple of bounces could have swept Chicago.
2019 was a brutal loss.