Sporting CP
On 2 July 2014, Sporting CP announced the signing of Gauld from Dundee United, for an undisclosed fee rumoured to be in the region of £3 million. He signed a six-year contract with a €60 million buy-out clause. He credited Sporting's track record of developing players such as Luís Figo, Cristiano Ronaldo and Nani for his decision to join them. Despite being put into the club's B-team, Gauld was named in the 25-man squad to play in the UEFA Champions League after impressing manager Marco Silva during training sessions.
He made his debut for Sporting B on 10 August 2014, replacing João Palhinha at half time in a 1–0 defeat away to Farense. Seventeen days later, in his fourth match for the club, he scored for the first time, netting the second in a 3–0 home victory over Aves. On 7 December, he scored a second goal, opening a 4–3 win at Lisbon neighbours Oriental with a 20-yard volley. On 21 December, he was sent off for two bookings in a 3–1 triumph at Vitória de Guimarães B. He finished the season with three goals from 26 games for the B-team, the third coming on 7 February 2015, when he equalised as the team came from behind to win 2–1 against Olhanense.
Gauld made his debut for the first team on 29 December 2014 in a Taça da Liga game against Vitória de Guimarães, playing the full 90 minutes in a 2–0 win. On his second start for the Sporting first team on 14 January 2015, Gauld was named man of the match in a 1–0 win in the same competition, against Boavista. Having been fouled by goalkeeper Daniel Monllor, he won the penalty converted by Junya Tanaka for the only goal. Four days later, he made his Primeira Liga debut, replacing André Martins for the last 25 minutes of a 4–2 win over Rio Ave at the Estádio José Alvalade. Gauld scored twice for the first team in a 3–2 defeat away to neighbours Belenenses in a Taça da Liga group game on 21 January.
In his second season in the Portuguese capital, Gauld scored his first goal of the B-team's campaign on 26 August 2015, the only one of the away match at Covilhã in the 84th minute. He followed this on 12 September with a strike in a 4–0 triumph at Oriental. Gauld matched his goal tally in Segunda Liga from the previous season on 3 October, when he opened a 1–1 draw at Famalicão, and succeeded it on 28 November with his fourth goal of the campaign, assuring the same result at Gil Vicente
On 20 July 2016, amidst interest from England's Sheffield Wednesday, Gauld was loaned to Portuguese top-flight team Vitória de Setúbal for the upcoming season, alongside his teammate André Geraldes. He made his debut for Vitória on 26 October 2016 in a Taça da Liga tie against lower-league Santa Clara, playing the full 90 minutes in a 2–0 win. He made his league debut three days later, coming on as a late substitute for Nenê Bonilha in a scoreless draw at home to Porto, his first game in Primeira Liga for 20 months.
On 5 January 2017, it was reported that Gauld had been recalled from loan to train with Sporting B, due to Sporting being eliminated from the Taça da Liga by Vitória in controversial circumstances. He played nine second-tier games for the B-team over the rest of the season, and was sent off on 14 May at the end of a 2–1 home loss to Académica de Coimbra.
On 24 July 2017, Gauld was loaned to Primeira Liga newcomers Aves. He was unable to play against his parent team on the first day of the season, however, he came on as an added-time substitute for Salvador Agra in the next game, a 2–2 draw with Paços de Ferreira on 13 August. In his fourth match on 11 September, he scored his first goal in Portugal's top flight, the winner in a 2–1 home win over Belenenses.
On 31 August 2018, Gauld joined LigaPro side Farense on a season-long loan. He scored his only goals for the Algarve club on 30 December, in a 5–0 home win over Oliveirense. The loan was curtailed in January 2019 and he was then loaned to Scottish Premiership club Hibernian. Gauld suffered a hamstring injury and consequently only collected 371 minutes of game time from six first team games in his half-season loan at Easter Road.
