The Boston Bruins have won the Stanley Cup six times, taking home the title in 1929, 1939, 1941, 1970, 1972, and 2011. However, they have also lost the Stanley Cup a league-high 14 times, once more than the Detroit Red Wings. While they haven’t always been able to get the job done in the final, Boston has made the Stanley Cup final the fourth-most times, trailing Montreal, Detroit, and Toronto.