In the 1967–68 season, Olmstead served as coach of the expansion Oakland Seals. Olmstead played in the Stanley Cup final in 11 of his 14 seasons in the NHL, winning it five times. He won it four times with Montreal, in 1953, and from 1956 to 1958, and once with Toronto, in 1962, which was his last season. He was inducted into the Hockey Hall of Fame in 1985.