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On 25 July 2019, Henderson signed a new contract with Manchester United until June 2022 and returned on loan to Sheffield United. He made his Premier League debut on 10 August as they began the season with a 1–1 draw at A.F.C. Bournemouth. On 28 September against Liverpool at Bramall Lane, he fumbled a shot from Georginio Wijnaldum for the game's only goal in the 70th minute. His manager Chris Wilder warned him that he would have to do better to succeed for Manchester United or England.

On 8 October 2019, Henderson was called up to the senior England squad for the first time by manager Gareth Southgate as a replacement for the injured Tom Heaton.

On 27 May 2019, Henderson achieved two Guinness World Records titles for 'Fastest time to dress as a goalkeeper (soccer)' (49.51 seconds) and 'Most football (soccer) headed passes in one minute (team of two)' (91 – with Jake Clarke-Salter).

By December, there were rumours when his parent club may recall Henderson in January. Later that month, Henderson kept three clean sheets in three matches against Blackpool, Portsmouth and Wigan Athletic. However, Henderson served a three match suspension after being involved in an altercation with an opposition supporter during a 3–1 loss against Blackburn Rovers on 13 January 2018. Initially the club made a decision to appeal, the club changed their mind shortly after. After serving a three match ban, Henderson returned to the starting line-up on 13 February 2018, in a 2–1 win over Fleetwood Town. By the end of March, Henderson kept 13 clean sheets for the team.

On 8 April 2018, he played at Wembley Stadium in the EFL Trophy final against Lincoln City, which Shrewsbury Town lost 1–0, and later that month was one of only three players not from Wigan Athletic or Blackburn Rovers to be selected for the League One PFA Team of the Year. The following month, in the League One play-offs, Henderson kept two clean sheets in a 2–0 win over Charlton Athletic on aggregate to reach the final. Henderson started in goal in the final when Rotherham United beat Shrewsbury Town 2–1 after extra time, and he saved a penalty from David Ball after nine minutes.

In June 2018, Henderson signed a two-year contract extension with his parent club, which was due to expire in June 2020. On 18 June, he joined Championship club Sheffield United on loan until the end of the 2018–19 season, helping them to secure promotion to the Premier League for the first time since 2007. During his season-long loan, Henderson won the club's Young Player of the Year Award, as well as the Championship Golden Glove.

He made his under-21 debut on 24 March 2018, in a friendly at home against Romania, which England won 2–1. Henderson was named as England's number one for the 2019 UEFA European Under-21 Championship.

It was then extended again on 25 January 2017, until the end of the 2016–17 season. However, Manchester United recalled Henderson from the loan spell on 3 February 2017, due to an injury to third-choice goalkeeper Joel Castro Pereira. By the time of his departure, Henderson made 7 appearances and kept 4 clean sheets; by the time of his departure, he was the first choice goalkeeper.

On 10 July 2017, Henderson joined League One club Shrewsbury Town on loan for the 2017–18 season. Upon joining the club, Henderson was given a number 1 shirt ahead of the new season.

In August 2017, Henderson was called up by the under-21 for the first time and appeared as an unused substitute bench against Latvia U21. He then appeared two more times as an unused substitute bench that saw him missed out two matches for the team in the league.

On 12 January 2016, he was loaned to National League North club Stockport County on an initial one-month loan. He made his Stockport County debut, where he played the whole game, in a 1–1 draw against Nuneaton Town on 16 January 2016.

On 22 February 2016, due to an injury crisis, Henderson was recalled from loan and had his first call-up to a senior Manchester United game, sitting on the bench during a 3–0 FA Cup victory away to Shrewsbury Town.

Henderson then returned to Stockport County to complete his loan spell. His first game after signing for the club for the second time was a 2–0 loss against North Ferriby United on 26 March 2016. He went on to make nine appearances for Stockport County and kept three clean sheets.

On 31 August 2016, Henderson joined League Two club Grimsby Town on loan until the beginning of January 2017. However, he started his Grimsby Town career as second–choice goalkeeper behind James McKeown.

Henderson made his debut on 26 December 2016, in a 2–0 victory over Accrington Stanley at Blundell Park. After making his debut, his performance was praised by Manager Marcus Bignot. On 31 December 2016, Henderson had his loan at Grimsby Town extended until the end of January 2017. On the same day, he kept another clean sheet, in a 0–0 draw against Blackpool.

In late-August 2016, Henderson was called up by under-20 team for the first time.

Henderson made his England U20 debut, where he started as a goalkeeper, in a 1–1 draw against Brazil U20 on 1 September 2016. In May 2017, he was selected in the England under-20 squad for the 2017 FIFA U-20 World Cup. He made one appearance at the tournament, in a group stage match against Guinea, and was an unused substitute during England's victory against Venezuela in the final. After the match, Henderson described this an "unbelievable feeling".

Henderson signed his first professional contract with Manchester United in 2015 and extended it in 2018 for a further two years until 2022, but as yet has not played a first-team game for the club, having instead been loaned out to a number of other teams. Having played in various lower divisions, he made his Premier League debut with Sheffield United in 2019. He has represented England at under-16, under-17, under-20 and under-21 levels.

After progressing through the academy, Henderson was among 10 players to join the Academy squad for the 2013–14 season. He became a regular goalkeeper for the U18 team in the 2013–14 season. In the 2014–15 season, Henderson continued to impress as a regular goalkeeper for the U18 team, as he made 25 appearances but sustained an injury towards the end of the season. Nevertheless, he was among nominees for the Jimmy Murphy Young Player of the Year award but lost out to Axel Tuanzebe. In August 2015, Henderson signed his first professional contract with the club.

Henderson made his Shrewsbury Town debut, in the opening game of the season, where he kept a clean sheet, in a 1–0 win over Northampton Town. He also kept another clean sheet in a follow–up match, in a 1–0 win over AFC Wimbledon. Henderson quickly established himself as the club's first choice goalkeeper and became the club's fan favourite. He also has helped the club win the number of matches to help them go to the top of the table. By September, Henderson reflected his time at the club so far, saying he enjoyed playing football there and playing Saturday/Tuesday is excellent for his development.

Henderson joined the Manchester United academy aged 14, having spent six years at Carlisle United. He first joined the academy in August 2011.

Dean Bradley Henderson (born 12 March 1997) is an English professional footballer who plays as a goalkeeper for Sheffield United, on loan from fellow Premier League club Manchester United.