Upon the recommendation of Harry McNally, O'Keefe was appointed as manager of Cork City, a club in the League of Ireland Premier Division. He appointed former Blackpool coach Billy Haydock as his assistant, and signed Blackpool goalkeeper Phil Harrington for a small fee. Also coming out of retirement as a player, his team won the pre-season Munster Senior Cup. He then signed former Stoke City defender Alan Dodd on a month-long deal. O'Keefe also doubled up as the club's commercial manager, and he arranged four Sportsman's Dinner events, with special guests as Jack Charlton, Sir Alex Ferguson, Tommy Docherty, and Emlyn Hughes. The club finished in seventh place in 1987–88 and lifted the League of Ireland Cup. Cork were heading to another mid-table place finish in 1988–89 when O'Keefe was sacked. Cork terminated his contract to cut costs, as the directors were forced to subsidise the club out of their own pockets. Following his dismissal he turned out for Brian Kerr's St Patrick's Athletic in a handful of games.