Duff began his career in 1954 with the Toronto Maple Leafs. He was a key member of the team that won the Stanley Cup in 1962 and 1963. He was also part of the team that won the Stanley Cup in 1967. During his time with the Maple Leafs, he scored over 200 goals and was named to the NHL All-Star team in 1964.
In 1968, Duff was traded to the Montreal Canadiens and was part of the team that won the Stanley Cup in 1971. He was also part of the team that won the Stanley Cup in 1973. During his time with the Canadiens, he scored over 100 goals and was named to the NHL All-Star team in 1969.
In 1975, Duff was traded to the Los Angeles Kings and was part of the team that made it to the Stanley Cup finals in 1976. He was also part of the team that made it to the Stanley Cup finals in 1979. During his time with the Kings, he scored over 50 goals and was named to the NHL All-Star team in 1976.
In 1980, Duff was traded to the Buffalo Sabres and was part of the team that made it to the Stanley Cup finals in 1981. He was also part of the team that made it to the Stanley Cup finals in 1983. During his time with the Sabres, he scored over 30 goals and was named to the NHL All-Star team in 1981.
In 1984, Duff was traded to the New York Rangers and was part of the team that made it to the Stanley Cup finals in 1986. During his time with the Rangers, he scored over 10 goals and was named to the NHL All-Star team in 1984.
Throughout his career, Duff was known for his hard-nosed style of play and his ability to score goals. He was a key member of several Stanley Cup winning teams and was named to the NHL All-Star team five times. He was inducted into the Hockey Hall of Fame in 2006.
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