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Dean Henderson joined the Reds as a 14-year-old from Carlisle United in his native Cumbria.
Henderson spent six years with Carlisle after initially starting as an outfield player and he reportedly attracted attention from Chelsea and Newcastle United with his performances. An England youth international, he is rated as an outstanding prospect and was tracked by United from the tender age of 10. "Dean has the potential to become an excellent goalkeeper," commented Academy goalkeeping coach Alan Fettis. "He has that competitiveness about him and doesn’t want to be beaten at anything. It’s a very healthy attribute to have, of course." Henderson impressed throughout 2014/15 and was shortlisted for the Jimmy Murphy Young Player of the Year award that was won by Axel Tuanzebe. He made 25 appearances but sustained an injury towards the end of the campaign. The challenge was to step up to United's Under-21 side and hold down a place in goal at that level and his first impressions were certainly favourable. Henderson was outstanding in the Lancashire Senior Cup win over Rochdale and also performed well in the UEFA Youth Cup tie at PSV Eindhoven. However, he was injured in the return game against the Dutch side and spent a lengthy spell on the sidelines. A first loan move of his career was sealed in January 2016 when he joined nearby Stockport County and this first-team experience enabled him to build his confidence even further. There was a dramatic recall from the Hatters when David De Gea was injured and Joel Castro Pereira cup-tied, enabling Henderson to be named on the bench for the FA Cup win at Shrewsbury Town. Back at reserve-team level, another fine outing for the goalkeeper came in the 1-0 win at Blackpool in the Lancashire Senior Cup as he captained the team and kept a clean sheet. Henderson embarked on another temporary spell away from United when he joined Grimsby Town at the end of August 2016, initially until January 2017. After making his professional debut in the Mariners' 2-0 win over Accrington Stanley on Boxing Day, he played seven matches in total for the League Two club and was impressive enough to have his loan deal extended until May. However, the spell came to an unexpected end on 3 February 2017 when he was recalled by the Reds following an injury to Pereira who was third choice at the time behind De Gea and Sergio Romero. Henderson was part of the England squad that won the Under-20 World Cup in Slovakia in June 2017 - he was an unused substitute in the final as the young Lions beat Venezuela. He has since gone on to represent his country at Under-21 level and is regarded as one of the brightest goalkeeping prospects around. The 2017/18 season was a landmark one for the youngster as he performed magnificently for Shrewsbury Town throughout his loan spell, appearing twice at Wembley and earning a place in the PFA Team of the Year for League One. Immensely popular with the Shrews faithful, he helped the team go all the way to the play-off final, only to lose to Rotherham United, despite Henderson's fine individual display. The first outing at Wembley came in the EFL trophy but, again, it ended in disappointment as Lincoln City won 1-0. Nevertheless, the confident stopper enhanced his reputation considerably and continues to grow in stature. Seeing his long-term future at United, Henderson signed a new contract with the club on 14 June that will run until at least June 2020, with the option for a further year. However, such is the fierce competition for places in the goalkeeping department at all levels at United, he joined Championship side Sheffield United on loan for the 2018/19 season in search of more regular first-team football, on the back of his impressive stint at Shrewsbury. The move was an outstanding success as he won the Golden Glove for keeping the most clean sheets in the division and was a key part of the Blades' promotion to the Premier League. With his stock continuing to rise, he was England's no.1 in the Under-21 European Championship in the summer of 2019. On 26 July, the club announced that Dean had signed a new long-term contract with the Reds and returned to Sheffield United on another season-long loan, to gain valuable top-flight experience.