The currently active National Hockey League team with the most Stanley Cups won is the Montreal Canadians. They currently have 23, and they're followed by the Toronto Maple Leafs with 13. The third place team is the Detroit RedWings, with 11.
Also note that one of the Montreal Canadians Stanley Cup wins was pre-NHL, and the Toronto Maple Leafs wins are the wins accumulated in that organization. That counts the team's two previous titles, the Toronto Arenas and the Toronto St Pats.
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The team with the second most Stanley Cups is the Detroit Red Wings, with 11,although they haven't won a championship since 2008 Detroit Red Wings - Second - 11 cup championships. Toronto Maple Leafs - Third - 11 cup championships.
the Montreal canadiens have won the most in the history of the nhl, but the nhl wasn't the only league that to compete for the cup.
Red Kelly is the most successful NHL player who never played for Montreal. He won 8 Stanley Cups with Detroit and Toronto between 1950 and 1967.
I'm going to go out on a limb here, but I would have to say Montreal Canadiens. They have won the most Stanley Cups. I would assume that they haven't won everytime they made it to the finals. Which would lead me to believe they have appeared the most.
The Montreal Canadiens is the only team in NHL history to have won 5 Stanley Cups in a row. They accomplished that feat between 1956 and 1960 inclusively. They also won 4 straight cups from 1976 to 1979. Other streaks worth noting are the NY Islanders who won 4 cups in a row from 1980 to 1983. The Edmonton Oilers won 4 in 5 years (1984, 1985, 1987, 1988)The Montreal Canadiens from 1956 to 1960, winning 5 Stanley Cups.