Kenny Shiels the League Cup Final, where they upset the odds by beating Celtic 1–0, with Dieter van Tornhout scoring the crucial goal in the 83rd minute. Killie's joy was tempered by the death of Liam Kelly's father, Jack, who suffered a fatal heart attack at the final whistle of the game. On the win, Shiels stated the team "are thinking more about Liam (Kelly) than our triumphalism". He then told BBC Scotland's Jonathan Sutherland, winning the cup is "unbelievable", in addition "a great emotion" for the Kilmarnock's supporters. Following his side's historic cup win, Shiels announced his intention to stay at
Dean Shiels NASL, Shiels returned to Scotland with Championship club Dunfermline Athletic. In November 2017, two players from Falkirk, Dunfermline's local rivals, were charged with 'excessive misconduct' for taunting Shiels over his visual impairment during a Scottish Challenge Cup fixture between the sides, following an incident during the match in which Shiels had been sent off. Both players were given lengthy suspensions. Shiels left Dunfermline at the end of his contract, having played 25 times for the side. Shortly after leaving Dunfermline, Shiels signed an 18-month pre-contract with League of Ireland Premier Division side Derry City, where he would once again play