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
Kenny Shiels several signings, the club, remained bottom of the league and a 2-0 loss against Alloa Athletic on 12 April 2014 confirmed relegation for Morton. Despite being relegated, it was initially believed that Shiels would stay on as the Greenock Morton boss for the next season, and attempt to return Morton to the Championship, similar to his experience during his time at Coleraine. However, Shiels resigned on May 2014 following a 10-2 defeat by Hamilton Academical which ended a poor season and relegation from the Scottish Championship. Immediately after the match, Shiels said in the post-match press conference, that he was