• OMJHL Second All-Star Team (1973)
• AHL First All-Star Team (1974)
• Won Dudley "Red" Garrett Memorial Award (Top Rookie - AHL) (1974)
• NHL Second All-Star Team (1982)
• Won Lady Byng Trophy (1982)
• Played in NHL All-Star Game (1981, 1982, 1984)

Rick Middleton began his professional hockey career as the first-round draft pick for the New York Rangers in 1974. He finished off the season with a flourish as rookie of the year in the American Hockey League, then played left wing with the Rangers for two years before he was traded to the Boston Bruins in 1976 for Ken Hodge. After a few years, sportswriters began calling it one of the most lopsided deals in recent hockey history, in favor of the Bruins. Things were looking pretty bright right from the start of Middleton's arrival in Boston, as he scored a hat-trick in his first-ever game as a Bruin.

Middleton was born in Toronto. He played his junior hockey for the Oshawa Generals and led the Ontario Hockey Association in goals his last season as an amateur. By 1985, Middleton had earned his place as captain of the Bruins. Middleton credits much of his success in hockey to Cherry, who very early in his career encouraged him to work on his defense. Without a doubt, Middleton was one of very few players in the NHL who was strong on both the power-play and as a penalty killer.

Middleton also gave credit to his wife and family for nurturing and maturing him, especially after he suffered a serious injury in mid-career after getting hit in the head with a puck in the days when not many NHL players wore helmets. "I used to lose my concentration a lot," he once admitted in reference to his maturing as a player. "And that became a big problem for me. Now I'm into the game more and I bear down harder."

In 1981 and 1984 Middleton was a member of the Canadian team in the Canada Cup. But his biggest success in international hockey, he claimed, happened in 1984 while he was a member of coach Scotty Bowman's team. Middleton played on a line with Wayne Gretzky and Gilbert Perreault. Gretzky himself was amazed at Middleton's abilities on ice.