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
Greenock Morton F.C. the relegation playoff by a single goal. Irons was sacked in September 2009 and replaced October by James Grady until the end of the season. Grady was removed from the club in May 2010, and replaced by Allan Moore. Allan Moore was sacked after a 5–1 defeat at home to Livingston on 23 November 2013. His replacement Kenny Shiels was given a contract until the end of season 2014–2015, but failed to reverse the slide towards relegation from the Scottish Championship, which became a reality on 12 April 2014 after a 2–0 away defeat by Alloa Athletic. Shiels resigned after