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 to join Rangers. He scored a goal, as well as, setting up two goals in his first appearance, in a Scottish League Cup tie against East Fife on 7 August. A week after he sustained an injury during a match which ruled him out for weeks, On 2 September 2012, Shiels scored his first league goal, as well as setting up a goal, in a 5–1 win over Elgin City. After scoring two goals in three games, Shiels scored against the Scottish Premier League side Motherwell, in a Scottish League Cup tie. Then, in the Scottish Cup, Shiels scored twice