Omagh native Caolan moved from Linfield to Partick Thistle in January 2012. Whilst he made the first team at Firhill, he moved out on loan to Airdrieonians. When his contract was up with Thistle he signed for East Fife and spent one season there before re-joining Airdrieonians. He then moved to Greenock Morton before returning to Ireland an signing for Harps at the beginning of the 2017 season. Caolan then singed for Sligo Rovers last season and has returned to Harps for 2019.
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