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Gary played with Wolves at youth level before beginning his senior career with Port Vale. A loan spell with Southport followed and then he joined Hereford United. Ahead of the 2015 LOI season he returned home and signed for UCD where he made four Europa League appearances. The following year he became captain and in 2018 led the Students to the First Division title, scoring 9 goals in the process.
Midway through 2019 he signed for Rovers alongside Neil Farrugia. He scored the winning penalty against Dundalk to win the FAI Cup that year, a moment Rovers fans will always remember. He also netted the winner against SK Brann in Europe. Many Rovers fans have said that he is one of the best signings the club has made in recent times and is very much a favourite amongst the fanbase.