Dylan Connolly

Dylan was a member of the Bohemians U19 squad for the 2012/2013 season and he made his league debut for the Gypsies on 19 October 2012 when he came on as a late substitute in a 4-1 win over Bray Wanderers. That was his only league appearance for Bohs and in February 2013 he made the short move to Tolka Park to join Shelbourne's U19 squad. His league debut for the Reds came as an 88th minute sub against Shamrock Rovers on 30 August 2013 and he made 5 league appearances that year as Shels were relegated from the Premier Division.

The drop to the First Division opened the door for Dylan and he scored his first league goal for Shels on the opening weekend of the 2014 season. He went on to top the club's goal-scoring charts with 12 league strikes from 22 league appearances as the Reds narrowly missed out on promotion.

On 5 February 2015 Dylan signed for Mick McCarthy at Ipswich Town. He played mostly for the u21 squad at Ipswich, but did appear on the bench in four Championship fixtures towards the end of the 2014-15 season. In December 2015, Dylan left Ipswich by mutual consent and a few days later he signed a two-year deal with Premier Division club Bray Wanderers for the 2016 and 2017 seasons. Dylan played in 31 of Bray's 33 league games in 2016 and scored four times, prompting speculation that champions Dundalk were keen to bring him to Oriel Park for 2017.

Dylan finally completed that move to Dundalk in July 2017 as Bray entered financial difficulty.

In January 2019, Wimbledon signed Dylan from Dundalk for an undisclosed fee. Dylan was released by Wimbledon in June 2020.