Hollingworth was born in Montreal, Quebec. He played junior hockey with the Montreal Junior Canadiens and began his professional career with the Montreal Royals of the Quebec Hockey League in 1953-54.
A defensive defenseman, he started his National Hockey League career with the Chicago Black Hawks in 1954. That season he recorded 12 points while playing in all 70 games for the Black Hawks. He was involved in a blockbuster trade on May 28, 1955, moving to the Detroit Red Wings with Dave Creighton, John McCormack and Jerry Toppazzini in exchange for Tony Leswick, Glen Skov, Johnny Wilson and Benny Woit.
Hollingworth played parts of three seasons with the Red Wings and left the NHL after the 1958 season. He finished his career in the American Hockey League with the Cleveland Barons and the Hershey Bears.

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