Kenny Shiels Rangers in 17 years on 27 November 2011, in a 1–0 victory at Rugby Park, with a Manuel Pascali goal in the 80th minute. After the match, Shiels said a win over Rangers was a "fantastic win" for the club, in addition, stated his opinion that people in Ayrshire, who are Old Firm supporters, are not real supporters for Kilmarnock. He wrote in his Daily Record columns that he was critical of fans would watch the Old Firm, rather than their local team. In the January transfer window, Shiels soon added his son, Dean, and Ben Gordon. He also helped
Dean Shiels cost-cutting that is due to take place at the club; manager Ally McCoist refuted this. On 8 February 2014, Shiels scored a hat-trick in the Scottish Cup, as Rangers won 4–0 against Dunfermline Athletic. On 10 June 2016, Shiels left Rangers after his contract came to an end. He had made 43 appearances for Rangers in his final season with the club, as they won promotion to the Scottish Premiership. On 25 August 2016, Shiels signed for Dundalk in the League of Ireland Premier Division citing the "lure of European football" as one of the things that attracted him to