In 1889 O'Shea was appointed captain of the Dublin senior hurling team. That year his team only had to play one game to be declared provincial champions. After defeating Wexford O'Shea's team were give a walkover by Laois in the Leinster final. Dublin's next game was an All-Ireland final meeting with Clare. All did not go to plan as O'Shea's side trailed by 1-5 to 1-0 at the interval. Heavy rain spoiled the match and made the surface very slippery as the Clare men played in their bare feet. Dublin fought back in the second-half with three goals by W.J. Spain. A full-time score of 5-1 to 1-6 gave Dublin the title and gave O'Shea an All-Ireland winners' medal.