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
David Hopkin Anderson. As well as continuing as manager of the Development squad, he became assistant manager to the newly appointed boss Kenny Shiels. Hopkin took Shiels place as match-day interviewee after Shiels became unable to do so on medical advice. Hopkin resigned as assistant manager of Morton in April 2014. Hopkin left his post as reserve team manager to become assistant head coach at Livingston to Mark Burchill. Hopkin took temporary charge of the Livingston first team, after Burchill left the club, in December 2015. After three games, Livingston appointed Hopkin as head coach until the end of the 2015–16 season.