Nine!
Boston Bruins - 1941, 1970
Detroit Red Wings - 1943, 1952, 1997, 1998
Montreal Canadiens - 1944, 1960, 1968, 1969, 1976
Toronto Maple Leafs - 1948, 1949
NY Islanders - 1982
Edmonton Oilers - 1988
Pittsburgh Penguins - 1992
NJ Devils - 1995
Colorado Avalanche - 1996
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Yes, many teams have been swept in the first round. None were swept in the first round of the 2012 Stanley Cup playoffs. The last team to be swept in the first round was the Phoenix Coyotes, who were swept by the Detroit Red Wings in the 2011 Stanley Cup Playoffs.