Montreal Canadiens 1956-1960 are the only team to win five Cups in a row.
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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.
Jari Kurri has won 5 Stanley Cup Championships. He won all five cups with the Edmonton Oilers in 1984, 1985, 1987, 1988, and 1990.
5 Stanley cups were won on June 11 Montréal 1993 Colorado 2001 New Jersey 2003 Chicago 2010 L.A. 2012
Wayne Gretzky, Jarri Kurri
The Pittsburgh Penguins have won the Stanley Cup 3 times and have won over 2,300 regular season games