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
Dean Shiels NASL, Shiels returned to Scotland with Championship club Dunfermline Athletic. In November 2017, two players from Falkirk, Dunfermline's local rivals, were charged with 'excessive misconduct' for taunting Shiels over his visual impairment during a Scottish Challenge Cup fixture between the sides, following an incident during the match in which Shiels had been sent off. Both players were given lengthy suspensions. Shiels left Dunfermline at the end of his contract, having played 25 times for the side. Shortly after leaving Dunfermline, Shiels signed an 18-month pre-contract with League of Ireland Premier Division side Derry City, where he would once again play