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 lost consecutive matches to Limavady United in the Gold Cup and Linfield in the league, causing Shiels to tender his resignation. According to the official club website Shiels was manager of Moyola Park from January 1999 to December 2000, although these dates overlap in part with his time at Coleraine. Nonetheless Shiels was in charge of the club and even signed a youthful Ivan Sproule for them. Shiels next appointment was at Ballymena United, where he was confirmed in the managerial chair on 2 January 2001. The club were battling relegation and ultimately Shiels was unable to prevent the club