In December 2013, Gunning said that he was looking at signing a new contract with Dundee United. On 29 January 2014, Gunning suffered a knee injury during training. He made his return against Motherwell on 21 February, where he scored twice as Dundee United won 3–1. This was the start of a run of four goals in three games for Gunning as he followed up those two with a goal on 28 February, in a 3–1 win over Hibernian and then another one in the quarter-final of the Scottish Cup, in a 5–0 win over Inverness Caledonian Thistle on 9 March. In the Scottish Cup semi-final against Rangers, Gunning set up Dundee United's first goal, scored by Stuart Armstrong, in a 3–1 win. In the Scottish Cup Final, Gunning started at centre back, alongside Seán Dillon, as Dundee United lost 2–0 to St Johnstone at Celtic Park.