The Montreal Canadiens lost to the Detroit Red Wings.
1935: Montreal Maroons defeated Toronto Maple Leafs 1947: Toronto Maple Leafs defeated Montreal Canadiens 1951: Toronto Maple Leafs defeated Montreal Canadiens 1959: Montreal Canadiens defeated Toronto Maple Leafs 1960: Montreal Canadiens defeated Toronto Maple Leafs 1967: Toronto Maple Leafs defeated Montreal Canadiens 1986: Montreal Canadiens defeated Calgary Flames 1989: Calgary Flames defeated Montreal Canadiens
Never, there was no such team as the Chicago Oilers. The Chicago Blackhawks have won the Stanley Cup five times (1934, 1938, 1961, 2010, and 2013). The Edmonton Oilers have won the Stanley Cup five times as well (1984, 1985, 1987, 1988, and 1990)
no, they went to finals in 1993 against Montreal Canadiens but lost
1980: lost in Quarterfinals (2nd round) to New York Islanders, 4 games to 1 1981: lost in Preliminary Round (1st round) to Minnesota North Stars, 3 games to 0 1982: lost in Adams Division Finals (2nd round) to Quebec Nordiques, 4 games to 3 1983: lost in Prince of Wales Conference Finals (3rd round) to New York Islanders, 4 games to 2 1984: lost in Adams Division Semifinals (1st round) to Montreal Canadiens, 3 games to 0 1985: lost in Adams Division Semifinals (1st round) to Montreal Canadiens, 3 games to 2 1986: lost in Adams Division Semifinals (1st round) to Montreal Canadiens, 3 games to 0 1987: lost in Adams Division Semifinals (1st round) to Montreal Canadiens, 4 games to 0 1988: lost in Stanley Cup Finals (4th round) to Edmonton Oilers, 4 games to 0 1989: lost in Adams Division Finals (2nd round) to Montreal Canadiens, 4 games to 1
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.
The most recent Canadian team to win the Stanley Cup was the 1993 Montreal Canadiens. Five Stanley Cup Finals since then have had a Canadian team lose to an American team: 1994 New York Rangers defeated Vancouver Canucks, 2004 Tampa Bay Lightning defeated Calgary Flames, 2006 Carolina Hurricanes defeated Edmonton Oilers, 2007 Anaheim Ducks defeated Ottawa Senators, and 2011 Boston Bruins defeated Canucks. The last Finals to be played between two Canadian teams was in 1989, when the Calgary Flames defeated the Canadiens.
Don Cherry doesn't have a Stanley Cup ring. He lost to the Montreal Canadiens in both of his appearances in the Stanley Cup Finals (1977 and 1978) as coach of the Boston Bruins.
3 times: 1986, 1989 (win), and 2004. Additionally the 1924 Calgary Tigers of the WCHL lost while playing the Montreal Canadiens for the Stanley Cup.
10. 1921-22 season: (Then called the Toronto St. Patricks) lost in one-game NHL Finals by a score of 7-0. 1924-25: (Toronto St. Patricks) lost one-game finals 5-2 to the Montrael Canadiens. 1932-33: (called Toronto Maple Leafs) lost Finals series to the New York Rangers, 3-1. 1934-35: lost series to the Montrael Maroons, 3-0. 1935-36: lost series to the Detroit Red Wings, 3-1. 1937-38: lost series to the Chicago Black Hawks, 3-1. (not called Blackhawks until 1987) 1938-39: lost series to the Boston Bruins, 4-1. 1939-40: lost series to the New York Rangers, 4-2. 1958-59: lost in series to the Montreal Canadiens, 4-1. 1959-60: lost in series to the Montreal Canadiens, 4-0.
The last team representing a Canadian city to win the Stanley Cup was the Montreal Canadiens in the 1992-93 season.The last Canadian hockey team to win the cup was the 1992-1993 Montreal Canadians. Guy Carbonneau was the captain.
There worst lost was against the timberwolves