1993 when they beat the L.A. Kings in 5 games
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Andrei Kovalenko of the Montreal Canadiens
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
1954: Tony Leswick helped Detroit Red Wings defeat Montreal Canadiens
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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.