55. Most of them were during the early Challenge Cup years, when the Cup was to be awarded to "the best amateur hockey team in Canada", as Lord Stanley originally intended. The last two Canadian teams to play for the Cup were the Calgary Flames and Montreal Canadiens in 1989. Calgary won in 6 games.
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Montreal Canadiens - 4 vs Chicago Blackhawks - 3
The Montreal Hockey Club defeated the Ottawa Hockey Club on March 22 1894 to be the first team to win the Stanley Cup.
Marian Hossa (now of the Chicago Blackhawks), played in the 2008 Stanley Cup Finals for Pittsburgh (and lost), played in the 2009 Stanley Cup Finals for Detroit (and lost), and played in the 2010 Stanley Cup Finals for Chicago (and won).
Most non-Canadian hockey players have been drafted from American teams to the Canadian teams.
West Indies vs. Australia