Randy Cunneyworth's journey in professional hockey began when he was drafted by the Buffalo Sabres in the eighth round of the 1980 NHL Entry Draft. Born in Etobicoke, Ontario, Cunneyworth developed his skills in the Ontario Hockey League (OHL) with the Ottawa 67's, where he demonstrated his potential as a left winger. His time in the OHL laid the foundation for his entry into the National Hockey League (NHL).

Cunneyworth made his NHL debut with the Buffalo Sabres during the 1981-82 season. Although his initial years in the league were spent moving between the NHL and the American Hockey League (AHL), he gradually established himself as a reliable player. His tenacity and work ethic on the ice were evident, and he became known for his gritty playing style.

In 1985, Cunneyworth was traded to the Pittsburgh Penguins, where he spent several productive seasons. It was with the Penguins that he began to gain more recognition, playing alongside emerging stars and contributing to the team's efforts. His role as a left winger was characterized by his physical play and ability to support both offensively and defensively.

Cunneyworth's career took another turn when he joined the Winnipeg Jets in 1989. His time with the Jets was brief, and he soon found himself with the Hartford Whalers. However, it was his subsequent move to the Ottawa Senators in 1992 that marked a significant chapter in his career. As a member of the Senators, Cunneyworth was named team captain, a role he embraced with leadership and determination. He played with the Senators during their formative years in the NHL, helping to guide the young team through its early challenges.

After his stint with the Senators, Cunneyworth continued his NHL career with the Chicago Blackhawks and later the Buffalo Sabres, returning to the team that had initially drafted him. His playing career concluded with the Rochester Americans in the AHL, where he also began to transition into coaching.

Following his retirement as a player, Cunneyworth embarked on a coaching career. He served as head coach of the Rochester Americans, where he applied his extensive knowledge of the game and leadership skills. His coaching tenure with the Americans was marked by a focus on developing young talent and fostering a competitive team environment.

Cunneyworth's coaching career also included a role as an assistant coach with the Atlanta Thrashers and later with the Hamilton Bulldogs, the AHL affiliate of the Montreal Canadiens. In 2011, he was appointed interim head coach of the Montreal Canadiens, a position he held until the end of the season. His time with the Canadiens was a challenging period, as the team faced various obstacles, but Cunneyworth remained committed to his coaching responsibilities.

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