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 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