Kenny Shiels guide Killie to the League Cup semi-finals, beating rivals Ayr United. Despite the win, Shiels criticised rival team tactics, believing the club should have done more. On 18 February 2012, Kilmarnock beat Rangers 1–0, with Shiels' son Dean scoring in the 12th minute, making him the first Kilmarnock manager to beat Rangers twice in one season. After the match, Shiels said a win over Rangers was dedicated to the club's supporters and praised his son, who scored the only goal in the match, for his performance as "outstanding". On 18 March 2012, Shiels' Kilmarnock side travelled to Hampden Park for
Kenny Shiels League Cup in his first season in charge, but he was sacked in June 2013 after he had been frequently punished by the Scottish Football Association for making controversial comments. Shiels was appointed manager of Scottish Championship club Greenock Morton in December 2013, and resigned in May 2014. He became Derry City manager in 2015. Shiels spent his entire playing career in Northern Irish football, both in the Irish Football League and at lower levels. Beginning at minor club Bridgend United, he subsequently appeared for Tobermore United, Coleraine, Distillery, Tobermore United again, Larne, Ballymena United, Tobermore United for a third