On 12 April 2014, Gauld played in the Scottish Cup semi-final at Ibrox, as United defeated hosts Rangers 3–1 to advance to the Final. He made the run into the penalty area from which Stuart Armstrong scored the opening goal, and assisted the second from Gary Mackay-Steven. Five days later, he was shortlisted for the PFA Scotland Young Player of the Year award, which was eventually awarded to his teammate Robertson. In the Cup Final on 17 May, Gauld replaced Mackay-Steven for the final 26 minutes as Dundee United lost 2–0 to St Johnstone at Celtic Park. Gauld's season ended with eight goals in 38 games across all competitions, of which six were scored in his 31 league matches.