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 embarrassed by the result and extremely disappointed with the performance. The scoreline was criticized by Dundee's manager Paul Hartley, whose team was promoted to the Scottish Premiership, comparing the scoreline to that of matches played in a pub league, while the chief executive, Scot Gardiner, would described the score line as "laughable" and "ridiculous". After a spell managing BEC Tero Sasana in Thailand, Shiels was appointed manager of League of Ireland club Derry City in November 2015. Shiels is the father of Northern Ireland international player Dean Shiels. Shiels is also the father-in-law of St Mirren manager Oran Kearney. His