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The Stanley Cup playoffs are underway as the second round has kicked off. With eight teams remaining, the chase for the Stanley Cup is alive and well.
Throughout the years some teams have had more success in the playoffs than others, while some have gotten to the Finals plenty of times but have lost.
Five NHL teams with most Stanley Cup Finals defeats
#1 Boston Bruins, 14
The Boston Bruins have lost 14 times in the Stanley Cup, which is the most in the NHL.
The Bruins last made the Stanley Cup in 2019 and lost to the St. Louis Blues in Game 7. Boston has made the Finals 20 times and has won the Cup just six times.
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#2 Detroit Red Wings, 13
The Detroit Red Wings have lost 13 times in the Stanley Cup Finals, with their most recent appearance being in 2009 when they lost to the Pittsburgh Penguins in Game 7.
Detroit had won the Stanley Cup the year before in 2008, beating the Penguins in six games. The Red Wings have won 11 Stanley Cups.
#3 Montreal Canadiens, 9
The Montreal Canadiens have lost nine times in the Stanley Cup, with their most recent loss in 2021 to the Tampa Bay Lightning.
Since losing to Tampa Bay in 2021, Montreal hasn't made the playoffs in three straight years. The Canadiens have won the Stanley Cup 24 times, which is the most in NHL history.
#4 Toronto Maple Leafs, 8
The Toronto Maple Leafs have lost eight times in the Stanley Cup Final but haven't made it to the Cup Final since 1967 when they last won the Stanley Cup.
Toronto's last loss in the Cup Final was in 1960 when they lost to the Montreal Canadiens.
#5 Chicago Blackhawks & New York Rangers, 7
The Chicago Blackhawks and New York Rangers are tied for fifth with seven losses in Stanley Cup Finals.
Chicago has won six Stanley Cups, and their last Cup appearance was in 2015 when they won. They last lost in the Cup Final in 1992.
The New York Rangers, meanwhile, won the Stanley Cup four times, while their last Stanley Cup Final appearance was in 2014 when they lost to the Los Angeles Kings.
