Background
O'Leary is the son of former Republic of Ireland international football player Pierce O'Leary and the nephew of David O'Leary.
O'Leary is the son of former Republic of Ireland international football player Pierce O'Leary and the nephew of David O'Leary.
O'Leary attended St. Aloysius' College, Glasgow.
He started his football career with Aberdeen and joined Kilmarnock for an undisclosed fee in 2005. After appearing sporadically for Kilmarnock due to injuries, Gordon Chisholm signed O'Leary for Dundee on loan until the end of the 2009–10 season. O'Leary left Kilmarnock when his contract expired in 2010 taking 9 months out of football for personal reasons.
In February 2007 he was named in a Republic of Ireland under-21 squad, but he declined, choosing to represent the country of his birth instead. He subsequently represented Scotland at under–21 level.