He began his professional career at Dundee United, where he helped them reach the 2014 Scottish Cup Final, and his abilities on the ball earned comparisons to Lionel Messi from the Scottish media. In July 2014, he transferred to Portuguese club Sporting CP for a fee of around £3 million. Gauld mainly appeared for the club's B team, and was also loaned to Vitória de Setúbal, Aves, Farense and Hibernian. In July 2019, Gauld moved to Farense on a permanent basis. In July 2021 he signed with MLS club Vancouver Whitecaps FC.