Stephen played for Galway United in the latter half of 2010 making 15 league appearances and scoring two goals. He made a further 31 league appearances in 2011 but it was a disastrous year for the Tribesmen and the club folded at the end of the season.
In January 2012 Stephen moved across the city to sign for Johnny Glynn at Mervue United. He played twenty league games for Mervue, scoring once. He re-signed for the club for the 2013 First Division. Stephen played another twenty-one games for the club, scoring seven goals in the season.
Stephen signed for the newly formed Galway FC for the 2014 First Division season and went on to make 23 league appearances for the club, scoring four goals, as well as playing in all four of Galway's play-off games against Shelbourne and UCD that led to promotion to the Premier Division.
Stephen stayed with the club for the 2015 season and added 28 league appearances, in a variety of positions, as Galway finished tenth in the Premier Division. He also played in the EA Sports Cup Final, which Galway lost on penalties to St Pats. In 2016, his third season after his return to Eamonn Deacy Park, he made a further 23 league appearances.
In January 2017 Stephen departed from Galway to sign for Alan Mathews at newly relegated Longford Town.