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
2005–06 in Scottish football football since the 1960s. Hearts became the first non-Old Firm club to win the Scottish Cup since they themselves lifted the trophy in 1998. Second Division side Gretna became the first club in history from the third-tier of Scottish football to reach the final. Celtic meanwhile lifted the League Cup in what was manager Gordon Strachan's first trophy as manager. St Mirren were winners of the Challenge Cup in a season that would eventually see them promoted to the SPL. Auchinleck Talbot lifted the Junior Cup. Scotland failed in their attempt to qualify for the 2006 World Cup, eventually finishing