O’Leary
returned to the K's in February 2022 as assistant to Hayden Bird and was
previously a popular member of the Kingstonian midfield between 2015 and 2017,
making 65 appearances in all and scoring 3 goals.
Before
his K`s playing days, he made 290 appearances for Hendon, scoring 27 times, in
a number of spells for the Greens after initially signing from Brook House in
2006.
He
also had stints as a player with Chertsey Town, AFC Wimbledon and Wealdstone,
and he had a brief spell at Canvey Island in between his two Kingstonian stays.
After
leaving Kingstonian, he moved to Potters Bar Town in 2017 and was a vital part
of their campaign that saw them promoted to the Isthmian League Premier
Division.
When
manager James Duncan left for Chesham United in October 2018, O’Leary stepped
up to become player-manager with Scott Cousins.
He
retired as a player and took charge as manager on his own and in 2019 took the
Scholars to their best ever run in the Emirates FA Cup when over 2,000 watched
them draw at home to Barnet in the Fourth Qualifying Round - a match streamed
live on the BBC Sport website.
He
resigned as Scholars` manager in January 2022 before being invited back to the
K's upon Jamie Howell's departure for Bognor Regis Town.
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