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 cost-cutting that is due to take place at the club; manager Ally McCoist refuted this. On 8 February 2014, Shiels scored a hat-trick in the Scottish Cup, as Rangers won 4–0 against Dunfermline Athletic. On 10 June 2016, Shiels left Rangers after his contract came to an end. He had made 43 appearances for Rangers in his final season with the club, as they won promotion to the Scottish Premiership. On 25 August 2016, Shiels signed for Dundalk in the League of Ireland Premier Division citing the "lure of European football" as one of the things that attracted him to