Stephen O'Leary is a skillful midfielder, who has spent time on-loan with Tranmere Rovers. Brian Little, the boss of the League One club at the time of O'Leary's arrival, became an instant fan of the central midfielder and went on to become a regular in the side, scoring three goals in 22 appearances. O'Leary joined Luton as a 13-year-old, when he was spotted playing for Barnet Schools and he was awarded a Scholarship in the summer of 2001 along with Kevin Foley. Luton had fought off competition from top London clubs for his signature and during his time with the Hatters he has also been a regular at schoolboy level for the Republic of Ireland. His game is a mixture of skill and determination, and he is equally at home going forward or in a midfield holding role. He was rewarded for his displays at the end of the 2006/07 season when boss Kevin Blackwell handed him a one-year contract.