On 18 February 2017, he scored 1-01 from play for St. Colman's in a 2-22 to 1-06 defeat by Our Lady's Secondary School from Templemore in the Harty Cup final.
Selected at left wing-back but mostly playing in a sweeper role, he ended the game with a second successive winners' medal after the 0-18 to 2-11 defeat of the Institute of Technology, Carlow.
[3] O'Leary joined the Castlelyons club at a young age and played in all grades at juvenile and underage levels.
[5] On 14 October 2018, O'Leary won a second successive Cork Senior Championship medal from centre-back, following Imokilly's 4-19 to 1-18 defeat of Midleton in the final.
[13] On 2 January 2019, O'Leary made his first appearance for the Cork senior hurling team in a 1-24 to 1-18 pre-season Munster League defeat by Waterford.