What team won the Stanley Cup the most times?

Answer 1

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.

Answer 2

The Montreal Canadiens have won the most Stanley Cups with 24.

Answer 3

If you mean which team it is the Montreal Canadiens with 24 titles. If you mean which player it is Henri Richard of the Montreal Canadiens with 11 Stanley Cup titles.

Answer 4

The Montreal Canadiens - 24 Stanley Cups.