Ryan was named SFL Young Player of the Month for February 2012,[4] and was given a three-year contract in March 2012.[5]
In June 2012, Ryan praised the club's youth set-up.[6] In September 2012, Ryan suffered an ankle injury.[7] At the start of the 2013–14 season, Ryan publicly stated that he was eager to prove his worth for new manager Alex Neil.[8]
On 18 October 2013, Ryan signed a one-month loan deal with Brechin City.[9] After returning to Hamilton, he admitted his chances at the club had been limited but he was still grateful to play there.[10] In April 2015 he signed a new contract with the club, until the summer of 2016.[11] On 13 August 2015, Ryan joined Arbroath on a three-month loan.[12] He left Hamilton by mutual consent in December 2015.[13]
After leaving Hamilton, Ryan played three matches as trialist for Arbroath, scoring once against Clyde.[14] He then signed for Forfar Athletic in January 2016.[15]
After a successful season with Airdrieonians, Ryan was signed for an undisclosed fee by Scottish Championship side Dunfermline Athletic on 15 August 2017.[17] On the same day, Ryan made his debut for the Pars in a Scottish Challenge Cup match against his former club Arbroath, scoring both goals in a two-nil victory at East End Park.[18] In January 2020 he returned to Airdrieonians on loan,[19] scoring twice in 7 appearances. In May he was released by Dunfermline at the end of his contract.[20]