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Barry joined Clyde in July 2017 and made his debut on the opening day of the season against his former side Annan Athletic. Barry began his career at St Mirren.

Primarily a central midfielder, Cuddihy spent most of the 2018-19 season at right-back and was voted as the Club’s Player of the Year as promotion was secured via the playoffs.

In April 2023 Barry made his milestone 200th appearance for the club, becoming just the 60th player in Clyde history to reach that number, and the first in 19 years.

Barry was appointed club captain ahead of the 2023-24 season.