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
The Minnesota Wild have not yet won a Stanley Cup.
No, he did not win the Stanley Cup.
The Penguins did not win the Stanley Cup in the 80's.
The Montreal Canadiens won their first Stanley Cup in 1916.
Chicago Stadium, Chicago
it was Anti Neimei
The New York Rangers first Stanley Cup championship came in the 1927-28 season.
The Ottawa Hockey Club (nicknamed the Senators) first won the Stanley Cup in 1903 when it was a challenge cup.The current version of the Ottawa Senators has not won the Stanley Cup.
In the 1934 Stanley Cup final, the Chicago Blackhawks beat the Detroit Red Wings in 4 games (3-1) to win their first Stanley Cup.