The Boston Bruins have the most series losses by a team in the Stanley Cup Finals, with 14 losses.

TEAM	SERIES L	PTS%
Boston Bruins	14	.393
Detroit Red Wings	13	.480
Montreal Canadiens	9	.630
Toronto Maple Leafs	8	.533

the Montreal Canadiens

Having lifted the trophy a total of 24 times, the Montreal Canadiens are the team with more Stanley Cup titles than any other franchise. Founded in 1909, the Canadiens are the longest continuously operating professional ice hockey team and the only existing NHL club to predate the founding of the NHL itself.There are 11 teams that have yet to win a Stanley Cup:

• Arizona Coyotes.
• Buffalo Sabres.
• Columbus Blue Jackets.
• Florida Panthers.
• Minnesota Wild.
• Nashville Predators.
• Ottawa Senators.
• San Jose Sharks.

Has the Stanley Cup ever been stolen : It seemed the most logical and safest place for such important pieces of history. But, in a piece of the NHL's lesser-known history, thieves stole the Stanley Cup, along with the Conn Smythe Trophy and the Bill Masterton Trophy, just a few years later.

Who has 13 Stanley Cups

Toronto Maple Leafs
The Montreal Canadiens have the most series wins by a team in the Stanley Cup Finals, with 23 wins.

TEAM	SERIES W	SA/GP
Toronto Maple Leafs	13	34.88
Detroit Red Wings	11	28.56
Chicago Blackhawks	6	30.76
Boston Bruins	6	29.79

What is the oldest NHL team without a Stanley Cup : The Canucks, along with the Sabres, are the two oldest teams in the NHL to have never won the Stanley Cup.

Jean-Guy Talbot (Seven Stanley Cups)

Among the current 32 active NHL teams, 11 have never won the Stanley Cup, with the oldest of them being the Vancouver Canucks and the Buffalo Sabres (52 seasons).

What is the least successful NHL team

The Winnipeg Jets have the lowest playoff winning percentage, (. 340). Additionally, the Boston Bruins lead all NHL franchises in playoff losses (341).Perry went on to lose his third consecutive Stanley Cup Finals with a third different team, becoming the first player in NHL history to do so.Don Cherry called into the program to defend Rodgers, stating his belief that he did not disrespect the Cup at all. On June 6, 2008, after the Red Wings' Stanley Cup Parade, the Stanley Cup was pushed off a table at Chris Chelios' Chili Bar in Detroit, Michigan and received a dent, which was later smoothed out.

Montreal Canadiens

Montreal Canadiens, Canadian professional ice hockey team based in Montreal. The oldest continually operating team in the National Hockey League (NHL), the Canadiens have won more Stanley Cup titles than any other team (24) and are the most successful franchise in league history.

Who has 11 Stanley Cup rings : Henri Richard

The most ever won by a single player was Henri Richard with 11 total championship rings.

Who won 5 Stanley Cups in a row : The Montreal Canadiens accomplished something that no other franchise has been able to match ‐ this dynasty won five consecutive Stanley Cup championships, first hoisting the Cup in 1956 and repeating each spring to 1960.

Who has the 2nd most Stanley Cups

Which team has hoisted the Stanley Cup the most times That would be the Montreal Canadiens, with 24 titles. Next are the Toronto Maple Leafs, with 13 championships, followed by the Detroit Red Wings, the winners of 11 Stanley Cups.

Mark Messier & 13 Players (Six Stanley Cups) Historically, there are 14 players to win the Stanley Cup an astonishing six times, with Glenn Anderson, Kevin Lowe, and Mark Messier being the last players to reach the plateau in 1994.Montreal Canadiens Canadiens de Montréal
Montreal Canadiens

Montreal Canadiens Canadiens de Montréal
Stanley Cups	24 (1915–16, 1923–24, 1929–30, 1930–31, 1943–44, 1945–46, 1952–53, 1955–56, 1956–57, 1957–58, 1958–59, 1959–60, 1964–65, 1965–66, 1967–68, 1968–69, 1970–71, 1972–73, 1975–76, 1976–77, 1977–78, 1978–79, 1985–86, 1992–93)

What’s the worst NHL record ever : The Montreal Wanderers, having had their arena burn down during the first NHL season, have the fewest games played (6), wins (1), and points (2), as well as the lowest point percentage (. 167).