Dylan played underage football for Swords Rovers and Malahide United before going to Middlesbrough at the age of sixteen. He spent two years at 'Boro but was released in the summer of 2013 when he returned to Ireland and joined up with Shelbourne's U19 side for 2013/14. In February 2014 he was named as part of Johnny McDonnell's first team squad ahead of Shelbourne's 2014 First Division campaign. Dylan made just 1 league appearance that year, coming on as a substitute in the final game of the season against Cobh Ramblers at St Colman's Park.

In January 2015, Dylan signed back with Shels for the 2015 season and went on to make 21 league appearances for the Reds during the First Division campaign, netting four times along the way, as Shelbourne finished fourth in the table. He was named in the PFAI First Division Team of the Year for his performances.

In December 2015, Dylan moved to Premier Division side St. Patrick's Athletic where he made his first league appearance away to Bray Wanderers on 23 April 2016. He made just 5 league appearances for Pats that year and in the winter break he left Richmond Park to sign for Alan Mathews at Longford Town. Dylan spent just six months at Longford, leaving the club at the end of June 2017.

In January 2019, Dylan signed with Bray Wanderers. In January 2021, Dylan signed back with Cork City for another season.