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
Dean Shiels his first hat-trick for Hibs on 12 January 2008 in a 3–0 win over Inverness Caledonian Thistle in the Scottish Cup, but Shiels struggled to establish himself as a Hibs first-team regular throughout his time at Easter Road. Shiels, whose contract with Hibernian was due to expire in the summer of 2009, signed for Doncaster Rovers on 2 February 2009. He was transferred for a fee of around £50,000. He made his Rovers debut on 21 February 2009, coming on as a second-half substitute in a 3–1 defeat at Swansea City. His first goal for the club came in the