Gary was part of the Sligo Rovers U19 squad for the 2013/2014 season and was named in Ian Baraclough's first team squad ahead of the 2014 league season. He made his league debut as a late substitute away to Derry City on 5 September 2014 and went on to play 8 times in the Premier Division as Sligo finished fifth in the league table.

In 2015 Gary made 21 league appearances for the Bit O'Red while still playing for the club's U19 side as Sligo finished ninth in the Premier Division. He scored his first league goal for the Bit o' Red in 2016, in a 1-1 draw away to St Patrick's Athletic, and finished the season with another 27 league appearances. Gary re-signed with Sligo for the 2018 season.

In January 2019, Gary signed for Cork City ahead of the 2019 season.