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After a long period out through an injury that required surgery, Winks returned to the squad in the 2018–19 season in the home game against Fulham, appearing as a late substitute. He made his first start of the season in the game against Liverpool that Spurs lost 2–1. In the away match against Fulham in January 2019, he scored a last minute winning goal to win 2–1, his first goal for the club since November 2016. On 1 June 2019, Winks started in the 2019 UEFA Champions League Final against Liverpool.

Winks signed a new five-year contract with Tottenham in July 2019.

Winks scored his first goal for England on 17 November 2019 in a 4–0 win against Kosovo in UEFA Euro 2020 qualifying.

Ex-England and Spurs midfielder Danny Murphy said in September 2018 that the England team should be built around Winks, citing his performance for Tottenham against Real Madrid in the 2017–18 UEFA Champions League group stage as evidence: "The one who I think has got the capability, more than anyone else I have seen, is [Harry] Winks. What he showed in that game in Madrid, in both games when he was fit and at it, was a confidence and an ability to play. To see the passes, to get his foot in and be disciplined and mix that mix of midfield talent that you need [...] for me, Winks is one of the best I've seen when he's at it – in terms of his all-round ability." ESPN FC' s Ben Pearce opined in 2018: "England are still missing a deep-lying playmaker [...] Those wondering who could possibly fill the void have obviously forgotten Winks, who excels at keeping possession with quick, short passes".

Winks began the 2017–18 season as substitutes in three early games after recovering from his injury. He made his first start of the season in the EFL Cup tie against Barnsley that finished 1–0. He next started in the match in UEFA Champions League away game against APOEL FC, and his performance earned him praise from Mauricio Pochettino as the "perfect midfielder". After only one previous start in the Premier League for the club this season (in a 4–0 win against Huddersfield Town) and four Premier League starts including last season, he gained his first call-up for the national squad. He received plaudits for his performance in the UEFA Champions League game away against Real Madrid where he was judged to have held his own against Luka Modrić and Toni Kroos. However, he picked up a niggling ankle injury in the match against Crystal Palace on 5 November 2017, which led to him missing final three months of this season after trying initially to play some games through the discomfort. He signed a new contract on 17 May 2018, keeping him at Tottenham until 2023.

On 2 October 2017, Winks received his first call up to the senior England squad, for their 2018 FIFA World Cup qualifiers against Slovenia and Lithuania. He made his debut when starting in England's 1–0 away win over Lithuania, which was the team's final match in their successful 2018 FIFA World Cup qualification campaign. Phil McNulty of BBC Sport stated that, on the night, Winks was "England's best performer. Neat and tidy and almost scored. Eye-catching among so much mediocrity". Winks missed the World Cup due to injury, but returned to the England squad in the 2018–19 UEFA Nations League away match against Spain. He helped England to a 3–2 win, the first competitive home defeat for Spain since 2003 and England's first win in Spain in 31 years, in what was judged a "self-assured" performance.

On 27 August 2016, he made his Premier League debut, replacing Christian Eriksen in the last minute of the match in a 1–1 draw at home to Liverpool.

On 19 November 2016, Winks made his full debut against West Ham United, performing well and scoring his first ever goal for Spurs to level the match at 1–1. Tottenham went on to win the match 3–2 in a dramatic finish at White Hart Lane after scoring two late goals. Winks made his debut in the FA Cup on 8 January 2017, when he was selected for the team in the match against Aston Villa of the third round. Tottenham went on to win the match 2–0. On 14 February 2017, Winks signed a new contract with Tottenham, keeping him at the club until 2022. During an away match against Burnley on 1 April 2017 in the Premier League, Winks suffered an injury when he tumbled into the Burnley dugout, and was later taken to hospital for a scan on his ankle. Spurs announced on 4 April that Winks would be sidelined by the injury to his ankle ligament for the rest of the season.

Winks has represented England up to senior level. Before this, he was eligible to represent Spain as well as England. He was part of the under-20 squad for the Mercedes-Benz Elite Cup in Germany in 2015. Winks made his under-21 debut on 14 November 2016 where he started in England's friendly 3–2 defeat to France.

On 6 July 2015, Winks signed a new contract with Tottenham until 2018, with the option of an additional year. He was given the number 29 shirt, which was included on the club's list of first-team numbers. Winks made his first appearance of the season as a late substitute in a 3–1 win against Qarabağ FK.

Winks is a product of the Tottenham Hotspur youth system. During the 2013–14 season, he regularly trained with the first-team squad and was named on the senior bench for the first time in a Premier League tie against Liverpool on 30 March 2014, remaining an unused substitute in a 4–0 loss at Anfield. On 27 July 2014, Winks signed his first professional contract with Tottenham; according to Winks, Mauricio Pochettino said that he wanted to sign Winks immediately after watching videos of his performances. He made his first team debut on 27 November 2014 in the UEFA Europa League group against FK Partizan in a 1–0 home win at White Hart Lane, replacing Paulinho after 87 minutes.

Winks plays as a central or defensive midfielder. Tottenham Hotspur manager Mauricio Pochettino has said "When we talk about midfielders – because you like to use Spanish midfielders like Xavi and (Andres) Iniesta – he's like this type of player", describing Winks as "completely different to our other midfielders like Victor Wanyama, Eric Dier, Mousa Dembélé and Moussa Sissoko. He has qualities to add to the team that are completely different". Talksport remarked that following his breakthrough for club and country, Winks was "seen as a potential difference-maker for the Three Lions due to his very individual skill set", with Winks earning comparisons with foreign midfielders rather than his English contemporaries.

Harry Billy Winks (born 2 February 1996) is an English professional footballer who plays as a central or defensive midfielder for Premier League club Tottenham Hotspur and the England national team.