Which NHL team has the most Stanley Cup Finals loses? 

The Boston Bruins, one of the NHL's Original Six teams and a franchise valued at $1.9 billion, hold the unfortunate record for the most losses in Stanley Cup Finals. Despite their rich history and numerous successes, the Bruins have come up short 14 times on hockey's biggest stage.

Since their inception in 1924 as the first American franchise in the NHL, the Bruins have established themselves as a powerhouse, winning six Stanley Cup titles and cementing their place among hockey's elite. However, their journey has been marked by heartbreaking defeats as well.

The Detroit Red Wings, another Original Six team, come in a close second with 13 losses in the Stanley Cup Final.

In 98 games in the Stanley Cup Final, the Bruins have a record of 37 wins, 58 losses and three ties. They have accumulated 77 points in these games, resulting in a points percentage of .393.

The team has scored 231 goals while allowing 265, and their power-play and penalty-kill percentages in the Final stand at 17.2% and 85.2%, respectively.

The Bruins' 14 Stanley Cup Final losses span several eras, from their early years in the league to more recent times.

Some of the most memorable defeats include the 2019 loss to the St. Louis Blues in a closely contested seven-game series and the 2013 loss to the Chicago Blackhawks, where they surrendered the lead in the final minutes of Game 6.

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Five worst Boston Bruins Stanley Cup final appearances

The Boston Bruins have had their fair share of disappointments in the Stanley Cup Final.

#1 1943: Detroit Red Wings vs. Boston Bruins (4-0)

Despite being the second-highest-scoring team in the league, the Bruins were outmatched by the Red Wings' defense. Boston scored only five goals in four games, losing twice by shutouts. It remains the franchise's worst showing in the final.

#2 1977: Montreal Canadiens vs. Boston Bruins (4-0)

The Canadiens had a historic season, becoming the first team to reach 60 wins and 132 points in an 80-game campaign. The Bruins were outscored 14-5 in the first three games and lost the series in a sweep.

#3 1988: Edmonton Oilers vs. Boston Bruins (4-0)

The Bruins failed to win a game despite having the fourth-most victories during the regular season.

The series is remembered for a power outage at the Boston Garden during Game 4, which was restarted in Edmonton. The Oilers won 6-3, completing the sweep.

#4 1957: Montreal Canadiens vs. Boston Bruins (4-1)

The Bruins and Canadiens finished two points apart in the regular season, but Montreal dominated the series. Boston scored only six goals in five games, with the Canadiens collecting two shutout victories.

#5 1990: Edmonton Oilers vs. Boston Bruins (4-1)

The Bruins faced the Oilers for the second time in three seasons but without Wayne Gretzky, Edmonton proved too strong. Despite finishing as the only team with more than 100 points in the regular season, Boston managed just one win and nine goals in the series.