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 from dropping down at the end of the season. Shiels responded by making a number of big name signings, including Tommy Wright, Paul Beesley and Liberian international Leon Browne, but none of them proved a success and the club finished in fifth place. The club improved significantly in the 2002–03 season, although ultimately they managed only second place in the First Division, as well as the Ulster Cup and the Country Antrim Shield. The league position was enough to ensure promotion, although the club had led the table until near the end when Dungannon Swifts took over at the top.