The Detroit Red Wings have won 11 Stanley Cups. They won in the following seasons: 1935-1936; 1936-1937; 1942-1943; 1949-1950; 1951-1952;1953-1954; 1954-1955; 1996-1997; 199…7-1998; 2001-200; 2007-2008. The Detroit Red Wings have won the Stanley Cup 11 times. The most recent win was 2008.