In March 1989, he came out of professional retirement to sign for Chester City, then managed by friend and former colleague Harry McNally. The signing was delayed due to lengthy negotiations with the Football League over his insurance payout from two years earlier. He was also appointed as the club's commercial manager, and attempted to form a football pool for the entire Football League, in conjunction with the FA and the "Daily Mirror"; however he could not break the Littlewoods monopoly due to a law that specifically banned newspapers from becoming involved in a pools game – O'Keefe believed that this arrangement "reeked of corruption". On the playing side, his Chester debut came at his former club, Blackpool, on 18 March 1989; he came off the bench to score in a 1–1 draw, denying Blackpool two points in their battle against relegation. Although he appeared in every game until the end of the season and became the club's penalty taker, O'Keefe only featured in three more matches in 1989–90 and drifted out of professional football circles, signing for Bangor City.