Luke Shaw became the most expensive teenager in the world when he moved to Manchester United for £30m in the summer of 2014.
The left-back had risen through the ranks at Southampton and, despite some injury setbacks, the England international has played some of his best football in recent years which has earned him a new deal at Old Trafford. It means, by the end of his contract, he'll have spent over a decade in Manchester.
He was signed by Louis van Gaal and has since played under Jose Mourinho, Ole Gunnar Solskjaer, Ralf Rangnick and now Erik ten Hag. Much has changed since his initial arrival, notably the personnel at the club, as they continue to refresh the playing group.
Shaw said after extending his stay: "Nine years ago, I signed for this amazing club, and I'm thrilled to be extending my stay." In his first year the club returned to the top four having previously dropped out with Shaw making his debut in a 2-1 win over West Ham several months after completing his move.
We take a look back at who played that day as well as who was in and around Carrington almost nine years ago.
David de Gea
One of the few who has lasted the course, De Gea has long been a rock behind Shaw, picking up numerous Player of the Year awards in Manchester. The Spaniard too is trying to negotiate a new deal at Old Trafford, but will have to take a pay cut on his hefty wages.
Rafael
The Brazilian begun blossoming under Sir Alex Ferguson and would remain in the squad under Van Gaal. However he would leave the next summer as the Dutchman shuffled his options, joining Lyon before going on to play briefly in Turkey. Rafael, now 32, has headed back to his homeland with Botafogo.
Marcos Rojo
He signed in the same summer as Shaw having impressed at the recent World Cup with Argentina, but never regularly produced in Manchester. Despite that he spent seven years at the club, playing sporadically, but now finds himself at Boca Juniors.
Paddy McNair
The versatile defender is one of several youngsters to be given an opportunity by Van Gaal early in his tenure. The Northern Irishman left Manchester in 2016 to join Sunderland, who would get relegated. He then made a short move to Middlesbrough, where he has been since 2018.
Daley Blind
Another player to be part of Van Gaal's first summer spree. Blind was known by the manager, who had just worked with him at the World Cup with the Netherlands. Incredibly talented on the ball, he played in midfield and defence but moved back to Ajax in 2018, now finding himself at Bayern Munich.
Ander Herrera
The Spaniard's stock had risen at Athletic Bilbao and eventually United pounced to secure his signature with the midfielder going on to play at Old Trafford for several years - winning Player of the Year in 2017. He opted to let his contract wind down and moved to PSG in 2019 but is now back in Spain at San Mames.
Angel di Maria
He became United's record-signing when he joined from Real Madrid in the summer of 2014, having just been named the Man of the Match in the Champions League final. The move never worked out however and within 12 months he was gone, heading to PSG, where he enjoyed notable success. Now he's trying to help Juventus get back to the top of Serie A.
Wayne Rooney
Shaw and the Evertonian were team-mates when Rooney became United's all-time leading scorer in 2017, but that would be near the end of their time together. Rooney went back to Goodison Park, then headed to Derby via the USA. Now he's back across the Atlantic, taking charge at DC United.
Robin van Persie
The forward was a huge success initially in Manchester, but only spent one year alongside Shaw under Van Gaal. He went to Fenerbahce and then headed back to Feyenoord, where he began his career. Van Persie called time on his career in 2019 and is now part of the coaching staff in Rotterdam.
Radamel Falcao
Among the biggest United flops, the striker's loan spell was a failure, albeit he rediscovered his best form when he returned to Monaco and continued to excel at Galatasaray. The 37-year-old is still plying his trade in Europe with Rayo Vallecano, where Brazil great Ronaldo is the owner.
Juan Mata
The Spaniard arrived six months before Shaw and spent just shy of a decade at United under a host of different managers. Mata's contract was allowed to expire in the summer of 2022 and he opted to head to Turkey, where he signed a one-year contract with Galatasaray.
Antonio Valencia
Signed by Ferguson as Ronaldo's replacement, the Ecuadorian was transitioned from a right winger to more of a right-back and continued to play under several different managers. He left in 2019, playing for two teams in his homeland, before opting to retire in May 2021.
Phil Jones
Another Ferguson signing, although his career has been ravaged by injuries, which has hampered him for almost a decade. Jones has played four games in the league in almost four seasons, but earned praise from Shaw himself upon his return against Wolves last term. His current deal expires this summer.
Michael Carrick
The midfielder has gone through a variety of roles since he first teamed up with Shaw. Carrick was coming towards the end of his career, but his impressive brain even saw him filling in at centre-half. Since retiring he's been an assistant - and a caretaker- at Old Trafford and is now leading Middlesbrough, who are in the hunt for promotion, as he manages former team-mate McNair.
Ashley Young
The winger turned wing-back ended up donning the captain's armband at Old Trafford before he left for Inter Milan in 2020, having made more than 260 appearances for the Red Devils. Young is now back in England having returned to Aston Villa, whom he played for before United.
