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 with the Ulster Cup and Coleraine underlined their credentials by winning this competition. They carried their form into the league, with Shiels' men sitting top of the league after eight matches. The club remained in the hunt for the league title until the end of the season when they were pipped for the honours by Crusaders. This was to be the high-water mark of Shiels' time at Coleraine as the club began to slip back into a more mid-table position, despite some comparatively heavy investment in playing staff. During the 1999–2000 season, things came to a head when the club