Terrance Richard "Dick" Duff - Born February 18, 1936 in Kirkland Lake, Ontario is a retired Canadian ice Hockey left winger, scout, coach and general manager.

- Stanley Cup Champion 1962, 1963 with Toronto Maple Leafs, 1965, 1966, 1968, 1969 with Montreal Canadiens.

- Prince of Wales Trophy Champion 1963 with Toronto Maple Leafs, 1966, 1968, 1969 with Montreal Canadiens.

Duff didn't play organized Hockey until his teen years, but never missed an opportunity to grab a stick and his skates and join in any number of games that were going on at any one time. "We played through the school system (St. Jerome School). We didn't play a lot of games, but we played a lot of Hockey. We could skate forever. I had all kinds of brothers (13 brothers and sisters) and we'd be playing back and forth with the neighbours until it got dark!"

Duff only really became serious in the sport at the age of 15. It was at this young age that he moved to Toronto to attend St. Michael's College School and play Hockey for the school affiliated team, now known as the Toronto St. Michael's Majors.

Duff split his first season between the Junior 'B' Buzzers and the Junior 'A' Majors, both based out of St. Michael's College.

Duff helped St. Michael's reach the finals of the 1953 J. Ross Robertson Cup Junior championship.

By the 1953-54 season, Duff was firmly established with the Majors, and went on to lead the team in both goals (35) and points (75). He led the team in scoring again in 1954-55, edging his brother with 53 points to Les's 51.

On March 10, 1955, Duff made his NHL Debut with the Toronto Maple Leafs in a scoreless tie vs Montreal Canadiens at The Forum. "The Maple Leafs would say, 'Put this guy with the pros. He's ready; he's strong enough, he's mentally strong enough and our team can absorb him now.'" He played 3 games for Toronto that spring.

Having earned the opportunity to play with the Maple Leafs, Duff surrendered his final season of junior eligibility and signed with Toronto at the age of 19. He scored his 1st NHL goal vs Jacques Plante of the Montreal Canadiens on October 26, 1955 at 16:25 of the 2nd period at Maple Leaf Gardens in a 2-1 Toronto win. Duff scored both the goals for the Maple Leafs, his second goal the game winner.

"I was playing on the first line that year. (Linemate) Tod Sloan got 37 goals and I got 18 goals and 37 points with 74 minutes in penalties. Dick was one of the central figures as the Maple Leafs re-built the team through the late-fifties, enjoying three consecutive seasons with 25 or more goals for Toronto between 1957 and 1959. The Maple Leafs made the playoffs his first season but missed out on post-season play in 1956-57 and 1957-58.

But as the decade turned, so did the fortunes of the Toronto Maple Leafs. "By the time 1958-59 showed up, we had a confident team. We had been guys looking for a little direction; a little confidence. Coach Punch Imlach gave that to us when he first came to Toronto.

Duff, now a assistant captain, played a pivotal role in the Stanley Cup championship won by the Toronto Maple Leafs in 1962. Although he missed more than a quarter of the regular season suffering from a broken ankle, Dick scored the Stanley Cup-winning goal on April 22, 1962, as Toronto edged Chicago 2-1 to win their first Stanley Cup since Bill Barilko and his teammates celebrated in 1951.

The Maple Leafs repeated their Stanley Cup championship in 1963, with Duff setting an NHL record that still stands by scoring two goals in the first 1:08 of Game One of the final on April 9, 1963. Duff scored at the 49-second mark and again 19 seconds later. Toronto would beat the visiting Red Wings 4-2.

On February 22, 1964, with the Maple Leafs in a slump going into the playoffs, the popular forward was packaged with Arnie Brown, Bill Collins, Bob Nevin and Rod Seiling and sent to the New York Rangers for Andy Bathgate and Don McKenney. Duff was named team captain for the Rangers.

On December 22, 1964, Duff was traded to the Montreal Canadiens with Dave McComb for Billy Hicke and the loan of goaltender Jean-Guy Morissette.

Too small to be considered a power forward, Duff still managed to play like one. The 5-foot-9, 165-pound left winger did everything expected of bigger forwards. He battled for the puck, carried it through traffic and staked a claim to his spot in front of the enemy net. Montreal coach Toe Blake had seen this in his playing style while in Toronto and said, 'Dick, I'm going to get you to play with Béliveau. Just watch near the blue-line. He's got the big long reach so don't be going offside."'

Having the chance to play for Montreal revitalized Duff's spirit and his play. With the Canadiens, Duff quickly became a fan favorite and an essential component of the Canadiens team that won the Stanley Cup in the spring of 1965, picking up nine playoff points along the way. He assisted on Béliveau's Stanley Cup winning goal.

Duff had a strong season in 1965-66, scoring 21 goals, 24 assists, then in the Stanley Cup finals he had 2 assists including on the game winner of pivotal game four to tie the series (2-2), 1 goal, 1 assist in game five and then Montreal took the 1968 Stanley Cup championship in OT of game six.

Long recognized as one of the NHL’s most dogged competitors, Duff took his game to another level when the stakes were raised. Among his 25 goals in 1967-68 season, 8 were a team-leading game winners. In the finals, he set up Bobby Rousseau for the game three OT winner and also got a goal in game four, as Montreal swept St. Louis 4-0 for the Stanley Cup championship.

In the spring of 1969, he enjoyed the best postseason of his lengthy career. Playing with the abandon of a youngster, he scored a team-leading six playoff goals and finished with 14 points, second only to team captain Jean Béliveau. In the finals, Duff scored in three of the championships games, including 2 goals, 1 assist in game 3. He had a point in every game.

Duff helped the Montreal Canadiens to the 1965, 1966, 1968, 1969 Stanley Cup Championships.

Duff never learned to speak French.

"It's the only regret I have," he said. "I was at Henri's house a couple of times after we won the Cup and his little guys were there and I would have liked to have expressed to his kids what their father meant to me and to the team. Henri Richard was small but he had the heart of a lion."

In January 1970, Duff was moved to the Los Angeles Kings for Dennis Hextall, then, in November, he was swapped to the expansion Buffalo Sabres with another former Maple Leaf, Eddie Shack, where they were reunited with former Toronto coach, Punch Imlach. Duff retired after eight games in the 1971-72 season.

Duff played in 1030 regular season NHL games, scoring 283 goals (38 GWG), 289 assists with 743 penalty minutes, and 114 NHL playoff games, scoring 30 goals (6 GWG / 1 OTG), 49 assists with 78 penalty minutes.

Maple Leafs coach Punch Imlach once said that Duff was "probably the best playoff player I ever coached."

Duff played in seven NHL All-Star Games, as well - 1956, 1957, 1958, 1962, 1963, 1965 and 1967.

Duff returned to the Toronto Maple Leaf organization in 1979-80 season, and before his retirement, served as a scout, an assistant coach and in 1980-81, was one of three men to coach the Toronto Maple Leafs. He also served as Maple Leafs co-general manager in 1987-88.

Dick Duff was inducted into the Hockey Hall of Fame in 2006.

Dick Duff was inducted into the Ontario Sports Hall of Fame in 2014.

St. Michael’s inducted Terrance Richard “Dick” Duff into The Order of St. Michael.