Skilful midfielder O’Leary joined Luton aged 13 and steadily worked his way up the youth and reserve team ranks
O’Leary’s Luton first-team debut came against Rushden & Diamonds in 2003. The effervescent, tough-tackling midfielder, who can play anywhere across the middle, went on to appear a further five times that season, scoring his first goal for the club against Sheffield Wednesday.
But after featuring more than 20 times on loan at Tranmere during the second half of 2005/06, O’Leary has struggled to nail down a regular berth in the Hatters’ starting 11.
He played in Luton’s 5-0 FA Cup defeat to Liverpool in 2008, but was called upon just 16 times in the league that campaign as Town succumbed to relegation.