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Armstrong signed a four-year contract with Southampton in June 2018. He said he wanted to "hit the ground running" at the club. In November 2018 he stated that he did not miss Scottish football.

Armstrong represented Scotland at under-19 and under-21 level, then made his full international debut in 2017. He was voted as the SFWA Young Player of the Year in 2013 and has been named in the PFA Scotland Team of the Year for the Scottish Premiership three times. He was also nominated twice for the PFA Scotland Young Player of the Year.

Celtic won a second successive domestic treble in 2017–18, but Armstrong's season was interrupted by injuries. In June 2018, Celtic agreed a £7 million transfer fee for Armstrong with Premier League club Southampton.

Armstrong enjoyed a productive 2016–17 season, scoring 17 goals in all competitions as Celtic won a domestic treble.

Armstrong scored once and claimed two assists in November 2014 in wins over Kilmarnock and Motherwell. Armstrong scored twice more in league victories in December 2014 against Ross County and Celtic. He also registered assists in back-to-back matches in December 2014, in the defeat of Celtic and then the league defeat to St Johnstone In January 2015, Armstrong claimed a further two league goals and three assists in victories against Dundee and Hamilton Accies and another league goal in a draw with St Mirren. His last match for Dundee United came in a New Firm derby defeat of Aberdeen in a 2014–15 Scottish League Cup semi-final on 31 January 2015. Armstrong made 150 appearances, starting 109 matches, and scored 22 goals in all competitions for Dundee United before joining Celtic.

In January 2015, Dundee United turned down two transfer offers from Celtic for Armstrong, however the transfer was completed on 2 February 2015, alongside fellow Dundee United player Gary Mackay-Steven. Armstrong denied requesting the transfer. Both players would be ineligible for the remaining Scottish Cup and Scottish League Cup ties as Celtic chased a domestic treble. Armstrong and Mackay-Steven were later given the nickname Zig and Zag by the staff at Celtic.

Armstrong scored on his Celtic debut in a 3–0 league victory at Partick Thistle on 11 February 2015. He gave Celtic a 2–0 lead after fellow debutante Gary Mackay-Steven opened the scoring. Armstrong made his Celtic Park and European debut in a 3–3 draw with Inter Milan in the UEFA Europa League on 19 February 2015.

Armstrong made his first appearance of the 2015–16 season, in the UEFA Champions League second qualifying round first leg tie against Stjarnan, assisting the second goal in a 2–0 home win. He scored his first goals of the season with a second-half brace, in a 4–2 league win against Inverness CT on 15 August. He claimed assists in back-to-back matches in January, in wins against Dundee United and Hamilton, the latter result was an 8–1 home victory, the biggest recorded league win since the formation of the Scottish Premiership in 2013. His next goal came in a 3–1 league defeat of St Johnstone four days later.

In 2014, Armstrong was studying for a law degree through the Open University in his spare time.

The next season, Armstrong made his European debut in the Europa League third qualifying round, second leg, which ended in a 5–0 loss against Russian side Dynamo Moscow. After making six appearance this season, Armstrong agreed a three-year contract with Dundee United in September 2012. Armstrong signed a new contract with United in October 2012. Armstrong scored his first goal of the season on 24 November, in a 2–1 win over Ross County. In mid-December, Armstong provided two assists in consecutive matches against Dundee and Inverness. Having made six appearances in February, Armstrong was awarded Clydesdale Bank Premier League Young Player of the Month. Armstrong was nominated for SPFA young player of the year, but it was awarded to Hibernian's Leigh Griffiths. He did, however, go on to win the SFWA Young Player of the Year award.

In the 2013–14 season, Armstrong started his season well, scoring goals against Hibernian and St Johnstone. Armstrong and Dundee United began negotiations over a new contract and on 12 December, he signed a one-year contract extension. Armstrong expressed an ambition to play in England in the future, but said he was happy to wait until he had established himself in the first team. In the January 2014 transfer window, the Daily Mail reported that Celtic were considering making a move for Armstrong, and that they were also interested in some of the club's other youngsters. This was later dismissed as "speculation" by Celtic manager Neil Lennon. In April 2014, he was nominated for the 2013–14 PFA Scotland Young Player of the Year award. He was also selected to the 2013–14 Premiership PFA Scotland Team of the Year.

Armstrong represented Scotland at under-19 and under-21 levels. On 21 May 2013, Armstrong was called up for the senior team, along with his Dundee United teammate Gary Mackay-Steven. He was called up again by the national team in August 2015, and again in March 2017. Armstrong made his full international debut on 26 March 2017, in a 1–0 win against Slovenia. National team manager Gordon Strachan called it "the best Scotland debut I have ever seen." In September 2017 he was ruled out of two 2018 World Cup qualifying games through injury.

Armstrong made his first team debut for Dundee United in November 2010, coming on as a substitute in a 1–0 win over Hamilton Academical. Two months later, on 12 January 2011, he provided his first assist, crossing for David Goodwillie to score as his side won 2–0 against Motherwell. Throughout the rest of the season, Armstrong was in and out of the team, making twelve appearance. Manager Peter Houston praised Armstrong on his substitute role.

The next season, Armstrong swapped between starting and coming off the bench as an impact sub. In a match against Inverness Caledonian Thistle, on 10 December 2011, he provided a double assist, in the second-half, to make a comeback win, which his side won 3–2. Armstrong then scored his first goal for United in a 2–2 draw against St Mirren in December 2011. After the match, Armstrong says scoring his first goal was his first proper strike, having scored but it was deflected against Inverness.

Armstrong began his career with Dundee United, making his debut in 2010 and going on to make almost 150 appearances. Armstrong moved to Celtic in February 2015, and helped them win four Scottish league championships and consecutive domestic trebles. He then moved to Premier League club Southampton in June 2018.

Armstrong played for Dyce Boys Club and the Inverness Caledonian Thistle youth team, before signing professionally with Dundee United in July 2009.

Stuart Armstrong (born 30 March 1992) is a Scottish professional footballer who plays as a midfielder for Premier League club Southampton and the Scotland national team.