Ryan played his youth days for
Belvedere before moving abroad. He started his professional career at
Sunderland making two substitute appearances in the
Premier League in 2003. His debut came in the
Tyne–Wear derby in April 2003. He signed for
Scunthorpe United initially on loan in March 2005. This became a permanent move in June. The following season he signed for
Boston United. He left the club a year later after their double relegation, intending to return to his native Ireland. Ryan signed for
Royal Antwerp in July 2007, making his competitive début in a 4–1 defeat to Kortrijk on 30 September, before moving back to
Sligo Rovers. He made his
League of Ireland debut for Sligo in a 1–0 defeat to Cork City at the Showgrounds on 3 August 2008. He scored his first goal for the club in a 2–2 draw with Cork City in the
2009–10 Setanta Sports Cup, Sligo's first ever goal in the competition. He struggled to get a regular place in the side for his first year and a half as he struggled with fitness but came into his own with a string of highly impressive passing displays in the successful 2010 season. Ryan was Player of the Month in October and won the 2010 PFAI Player of the Year award. He was named as club captain for the 2011 season and captained the club to a second-place finish in the league and an FAI Cup, which Sligo won after beating Shelbourne on penalties. This was Ryan's first time winning an FAI Cup as he was suspended for the 2010 Final. Ryan signed for
Scottish Premier League side
Dundee United in November 2011. He joined his new teammates in January 2012, making his debut as a substitute in a 2–1 defeat by
Aberdeen on 2 January. On 25 July 2013, it was announced that Ryan had left Dundee United by mutual consent. On 7 August it was announced that he had signed for
Shamrock Rovers. He made his league debut two days later. In September Ryan won his second
League of Ireland Cup. Ryan signed with
North American Soccer League club
Ottawa Fury FC on 10 December 2013. After two years with Ottawa, Ryan transferred to
Jacksonville Armada FC on 15 December 2015. Less than six-months later Ryan was on the move again, joining fellow NASL side
Miami FC on 13 May 2016, for a reported fee of $750,000. On 19 February 2018, Ryan signed with
USL side
FC Cincinnati. On 17 January 2019, Ryan signed with USL Championship side
El Paso Locomotive FC. He made 107 appearances for the club before his retirement following the
2022 season. == Coaching career ==