Kenny Shiels in May 2007, as their head of youth. He left Tranmere in June 2010 to become assistant manager at Kilmarnock, following his three-year stint at the club. After Mixu Paatelainen left Kilmarnock to become manager of the Finland national football team, Shiels became caretaker manager. His first game in charge was a goalless draw with St Johnstone on 2 April 2011. On 15 June 2011, he became manager of Kilmarnock on a permanent basis and upon being manager, he soon added Jimmy Nicholl as his assistant manager, who just quit Cowdenbeath. He helped Kilmarnock achieve their first home win against
Dean Shiels NASL, Shiels returned to Scotland with Championship club Dunfermline Athletic. In November 2017, two players from Falkirk, Dunfermline's local rivals, were charged with 'excessive misconduct' for taunting Shiels over his visual impairment during a Scottish Challenge Cup fixture between the sides, following an incident during the match in which Shiels had been sent off. Both players were given lengthy suspensions. Shiels left Dunfermline at the end of his contract, having played 25 times for the side. Shortly after leaving Dunfermline, Shiels signed an 18-month pre-contract with League of Ireland Premier Division side Derry City, where he would once again play