Place of Birth: Dublin, Ireland
Ian started off his career as a trainee at Leeds United and joined Blackpool on loan at the start of the 2005-06 season. He made thirty appearances for the League One club, scoring three goals that came in wins over future club Scunthorpe United and Doncaster Rovers. Blackpool staved off relegation that season with a nineteenth place finish.
Ian left Leeds after returning from his loan and signed for fellow League One side Scunthorpe United ahead of the 2006-07 season. He would make twenty-eight appearances, again scoring three times, as Scunthorpe won the League One title. He continued to be a mainstay of the side in the 2007-08 Championship season,playing a part in twenty-five league games, scoring three goals once more, as Scunthorpe were relegated in twenty-third place.
Ian stayed with Scunthorpe when they returned to League One and made twenty appearances for the club, scoring one goal in a 2-0 win over MK Dons, before leaving to join Carlisle United on loan in March 2009 until the end of the regular season. He played six league games for Carlisle as they survived relegation on the final day of the season and returned to Scunthorpe for the League One play-offs. He played in both legs against MK Dons as they won 7-6 on penalties, scoring the decisive ninth spot kick before Tore Andre Flo missed to send The Irons into the final. Ian played the whole ninety minutes as Scunthorpe won 3-2 and were promoted to the Championship once more.
In the 2009-10 season, Ian made two appearances for Scunthorpe in the Championship before joining League Two club Chesterfield in December on loan until the end of January. He made seven appearances for the club before returning to Scunthorpe, where he played once more in the Championship as the club finished twentieth.
Ian signed for Chesterfield on a season-long loan at the start of the 2010-11 season and played nineteen times for the side, scoring once, as they won the League Two title. In July 2011, Ian signed for Toquay United on a two-year deal and went on to make over fifty appearances for the League Two club. His two years at Torquay were in stark contrast to each other as in his first season, Torquay lost in the play-offs to Chesterfield while in his second season they just survived relegation by two points.
In June 2013, Ian signed for Northampton Town. He went on to make over forty appearances for the club over the next two years before leaving at the end of his contract in June 2015. In July 2015, St Patrick's Athletic announced that they had signed the left sided player and he finished the season with seven league appearances as well as scoring in the penalty shoot-out against Galway United as St Pats won the EA Sports Cup. He left the club at the end of the season.
Ian signed for Northern Ireland side Glenavon in March 2016 and made two league appearances for the club before leaving for Bohemians in July 2016. He made his debut for Bohs in the derby game against Shamrock Rovers on 15 July and had made 10 league appearances by the end of the season.
In December 2016, Stephen re-signed with Bohemians for the 2017 campaign. Ian re-signed with Bohs ahead of the 2018 season.
Ian then retired from playing football to become manager of Shelbourne at the age of just 31, ahead of the 2019 season.