Anthony Calvillo played for the Montreal Alouettes from 1998 until 2003. During that time, the Alouettes won three Grey Cups, in 2002, 2008, and 2009.
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Montreal Canadiens 1956-1960 are the only team to win five Cups in a row.
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.
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.
The two coaches are: Bud Grant Minnesota Vikings - Super Bowls IV, VIII, IX, XI (0-4) Winnipeg Blue Bombers - Grey Cups 1957, 1958*, 1959*, 1961*, 1962*, 1965 (4-2) Marv Levy Buffalo Bills - Super Bowls XXV, XXVI, XXVII, XXVIII (0-4) Montreal Alouettes - Grey Cups 1974*, 1975, 1977* (2-1) *- Win
The Montreal Canadiens won the Stanley Cup 5 times in the 1950s, in 53, 56, 57, 58, and 59,