O'Leary is a midfield player, who played across the midfield for Luton, but is said to prefer a central role. He has played for the Republic of Ireland at U16, U17, and 18 levels. He was involved in a Luton youth who produced a number of good players. He made his debut for Luton in November 2003, away at Rushden & Diamonds. In this season Luton went on to be crowned league 1 champions. During the 2005–06 season, he joined Tranmere Rovers on loan. He gave a great account of himself, and won the praises of supporters and then manager Brian Little. The Tranmere supporters called for him to be signed on a long-term contract, however after numerous offers from other clubs he choose to sign a new one-year contract at Luton in May 2007. He left Luton in 2008 after turning down a new contract offer as he wanted to play at a higher level.
On 27 August 2008 he signed for Hereford United on a one-year deal. He made his mark on his debut in the 2–0 home win over Crewe Alexandra by opening the scoring with a shot from 25 yards and setting up Bradley Hudson-Odoi for the second, collecting the man of the match award.[2] His period at Hereford was largely interrupted by injury. He left at the end of the season to join bradford city.
On 6 August 2009 O'Leary signed for Bradford City.[3] Again his season was disturbed due to a lengthy toe injury.[4] He left Bradford City at the end of the 2009–10 season with regret as he felt he never showed bradford fans his ability due to his injury.[5]
O'Leary joined Dunstable Town early in 2011–12, scoring a hat-trick in his second and final appearance before returning to Kettering Town. He then joined Hemel Hempstead Town in June 2012.[7]
Relatives
O'Leary's cousin is Noel O'Leary.
Notes
A. ab : Soccerbase has divided O'Leary's Bradford appearances between his own page[8] and a page for a non-existent "Steve O'Neill".[9] O'Leary's profile at Bradford City's website[10] confirms his debut in a match against Port Vale which Soccerbase attributes to "O'Neill", and Bradford City's statistics page confirms his total of seven appearances.[11]