Dundee United Gauld made his
Scottish Premier League debut as a 16-year-old, as an 87th-minute substitute for
Johnny Russell in the final match of the
2011–12 season, a 2–0 win away to
Motherwell on 13 May. On 24 January 2013, Gauld signed an extended contract keeping him at the club until January 2016. Later on in the
2012–13 season, on 1 April, he made his first start against
St Johnstone at
McDiarmid Park and marked the occasion with his first senior goal to open a game which ended 1–1. On 4 November 2013, during the
2013–14 season, Gauld's contract was further extended, to run until May 2016. Five days later, he scored twice in a 4–0 win against
Motherwell at
Fir Park. On 15 December 2013, the
Daily Record reported that
Manchester United's Scottish manager
David Moyes wanted to personally "
scout" Gauld, and take the opportunity to run the rule over the potential of other young Dundee United players such as defenders
John Souttar and
Andrew Robertson. However, the following day, also his 18th birthday, Gauld's contract was further extended until May 2017. Around the same time, he was being tracked by English
Premier League pair
Everton and
Liverpool, Italy's
Roma and Spain's
Real Madrid. 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. 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, 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 Loans 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. On 29 February 2020, he scored his first career hat-trick in a 3–1 win over
Académico de Viseu to put his team top of the second division; this concluded a run of six goals from seven games. Farense were granted promotion to the first division following the stoppage of the Portuguese second tier due to the
COVID-19 pandemic. Gauld finished the season as the team's top scorer and was voted as the top player in the Portuguese second tier. In the 2020–21 Primeira Liga, Farense were immediately relegated back, with Gauld their top scorer with another 9 goals.
Vancouver Whitecaps FC On 31 July 2021, Gauld signed with
Major League Soccer side
Vancouver Whitecaps FC on a three-and-a-half-year deal, becoming one of the club's
Designated Players. He scored his first goal for the Whitecaps on 21 August 2021 against
Los Angeles FC, an 89th-minute winner. In July 2022, he helped the Whitecaps win the
Canadian Championship and was awarded the
George Gross Memorial Trophy as the tournament's MVP. His figures for the
2022 Major League Soccer season were eight goals and nine assists, while the Whitecaps missed the
playoffs. Nineteen days later, Gauld was named MLS Player of the Matchday for Week 21 of the
2023 season, for recording a goal and two assists against Los Angeles. In November 2023, he was voted Whitecaps Player of the Season for the second consecutive year. On 25 January 2024, Gauld signed a three-year contract extension with the Whitecaps. On 23 February 2024, Gauld was named the 25th club captain in Whitecaps history, replacing
Russell Teibert. On 23 October, Gauld scored a hat-trick and assisted another goal in a 5–0 win over
Portland Timbers in the
MLS playoffs wild card round. In January 2026, it was announced that Gauld would miss the beginning of the
2026 season due to a knee injury. ==International career==