The Montreal Canadiens who have won the Stanley Cup 24 times!
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Montreal and Detroit
Marian Hossa (now of the Chicago Blackhawks), played in the 2008 Stanley Cup Finals for Pittsburgh (and lost), played in the 2009 Stanley Cup Finals for Detroit (and lost), and played in the 2010 Stanley Cup Finals for Chicago (and won).
The 1994 Stanly Cup Finals featured the Vancouver Canucks vs. the New York Rangers. The Stanley Cup was eventually won by the Rangers.
As of 2017, 20 of them.
The Toronto Maple Leafs have lost in the Stanley Cup Finals 8 times. Both the Montreal Canadiens and the Philadelphia Flyers have lost 6 times.