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As far as I can tell no Newfoundland native has ever been on a team that has won the Cup. Daniel Cleary who plays with Detroit has a good chance this year as the Red Wings are the best team in the League right now.
UPDATE: Good prediction! Dan Cleary, born in Carbonear, Newfoundland, did indeed become the first Newfoundlander to win the Stanley Cup with the Red Wings in 2008
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