With Jadon Sancho's future finally sorted, fans now know that his Manchester United nightmare is over after the winger completed a loan move to Chelsea. The deal, which contains a £25m obligation to buy at the end of it, means that the 24-year-old becomes yet another number in the incredibly bloated list of wingers that Todd Boehly has assembled.

Perhaps that is a good thing, as the erratic nature of the club may mean that very little is expected of Sancho as he tries to find a way to settle into his chaotic new surroundings. Once that happens, though, these are the players he will be attempting to try and emulate or do better than who have also worn the famous red and blue jerseys in their careers.

1 Mark Hughes

435 Man United appearances, 122 Chelsea appearances

One of the sweetest strikers of the ball and one of Manchester United's greatest-ever strikers, Mark Hughes was an absolute powerhouse up top who, alongside Eric Cantona, would help the Red Devils to their first-ever Premier League title in 1992.

Across two spells (1980-1986, 1988-1995), he scored 154 goals and helped the club win two domestic titles, three FA Cups, a League Cup, and produced a famous double to help lift the UEFA Cup Winners' Cup in 1991. When he moved to Chelsea in 1995, he brought his experience and tenacity, playing a key role in their FA Cup win in 1997, which ended a 26-year trophy drought.

2 Juan Mata

285 Man United appearances, 135 Chelsea appearances

Juan Mata arrived at Chelsea in 2011, instantly impressing fans with his flair, vision, and playmaking skills. He played a huge role in Chelsea's Champions League and FA Cup victories in 2012 and the Europa League win in 2013, earning him the club's Player of the Year twice.

In 2014, the World Cup winner moved to Manchester United, where he continued to deliver with his creativity and calm presence. He added an FA Cup, where he scored in the final, an EFL Cup, and the Europa League to his collection at Old Trafford. He became a fan favourite, not just for his ability but also for being one of the nicest guys in football.

3 Nemanja Matic

189 Man United appearances, 154 Chelsea appearances

Initially joining in 2009 before returning in 2014, Serbian midfielder Nemanja Matic had a far more fruitful time in London than he did in the North West. He became a key part of Chelsea’s midfield, known for his physicality and defensive skills, helping them win two Premier League titles in 2015 and 2017.

In the latter year, he reunited with Jose Mourinho at Manchester United, where he brought his experience and stability to the midfield, contributing to a 2018 second-place finish in the Premier League, but failed to win a trophy. Now at Lyon, the 36-year-old recently spoke out against the club's decision to sell his former teammate Scott McTominay.

4 Mason Mount

23 Man United appearances, 195 Chelsea appearances

Mason Mount joined Chelsea’s academy at six years old and rose through the ranks to become a key player by 2019. Known for his energy, creativity, and versatility, his crowning achievement came as he set up Kai Havertz for the only goal of the game to win the Champions League final in 2021. Unfortunately, injuries meant he fell out of favour at Stamford Bridge, leading to a £55 million move to Old Trafford in 2023.

Though early in his United career, it is the same old story for the England international, whose fitness issues have not allowed him to have an extended run in the team. Nevertheless, his success at the club he grew up at helps him place high on this list.

5 Ray Wilkins

177 Man United appearances, 106 Chelsea appearances

Nicknamed 'Butch' as a joke towards his more flamboyant dress sense, Ray Wilkins let his football do the talking on the pitch throughout his career. Known for his precise passing and calm demeanour, the midfielder was named club captain at just 18 years old.

In 1979, he would join United. At the Theatre of Dreams, Wilkins continued to shine, playing over 175 games and winning the FA Cup in 1983. His intelligent play and leadership on the field made him a respected figure at both clubs and in Italy for the likes of AC Milan. He would later return to Chelsea as a coach before his tragic passing in 2018.

6 Romelu Lukaku

96 Man United appearances, 59 Chelsea appearances

Very few players have racked up a combined transfer fee like Romelu Lukaku. Unfortunately, these expensive deals often failed to translate into much success at two of England's biggest clubs. Lukaku's career at Chelsea began in 2011, but he struggled for game time and was loaned out, later leaving permanently for Everton. After a successful spell there, he joined Manchester United in 2017, where he scored 42 goals over two seasons.

After a dominant stint at Inter Milan, the Belgian returned to Chelsea in 2021 with high expectations. However, immediate fall-outs and poor form meant that he quickly became a burden. In 2024, he secured a permanent move away to Napoli.

7 Paul Parker

139 Man United appearances, 4 Chelsea appearances

The go-to right-back before Gary Neville entered the picture, Paul Parker excelled in the early to mid-nineties for Manchester United. Known for his speed and defensive tenacity, he helped the team to two Premier League titles and the FA Cup in 1994, a 4-0 win against none other than Chelsea.

As Neville came in and made the spot on the right-hand side his own, Parker was shipped out to Chelsea for a short stint that lasted just four appearances. Had he managed to feature more prominently for them, he would likely finish higher on this list due to the success he had under Sir Alex Ferguson.

8 George Graham

42 Man United appearances, 94 Chelsea appearances

Most known for his time as a player and manager at Arsenal, George Graham’s playing days at Chelsea (1964-1966) saw him operate in the middle of the pitch, where he became a useful source of goals for the Blues.

Winning a League Cup in 1965, he moved to Manchester United in 1972, but his time at Old Trafford was less distinguished. Shortly after, his focus turned to management, where he would become one of the greatest bosses in Arsenal's history.

9 Mark Bosnich

38 Man United appearances, 7 Chelsea appearances

Mark Bosnich's career at Manchester United began in 1989, but he only played a handful of games before returning to Australia. He later returned to England with Aston Villa, and in 1999, rejoined United as one of Peter Schmeichel's successors. He got his chance in the first team after Massimo Taibi's failed stint in between the sticks.

Despite winning a Premier League title in 2000, his form was inconsistent, and he was later replaced. He moved to Chelsea in 2001 but struggled with injuries and off-field issues, leading to a five-year career break before he returned to football in his homeland. While Bosnich had the talent, his time at both clubs is often remembered more for what might have been than his performances on the pitch.

10 Juan Sebastian Veron

82 Man United appearances, 14 Chelsea appearances

Juan Sebastian Veron arrived at Manchester United in 2001 with high expectations, having dominated Serie A, which was widely considered to be the greatest league in the world. However, he struggled to adapt to the pace of the Premier League, showing flashes of brilliance but inconsistency overall, leaving him with a legacy as one of the worst signings in the club's history.

After two seasons of trial and error, he moved to Chelsea in 2003, but injuries limited his impact there too. While Veron’s time in England didn’t quite live up to his stellar reputation in Italy, he is still remembered for his technical skill and vision, even if his best days were seen elsewhere. At both clubs, Veron remains a "what if" story, hinting at what could have been.

11 Radamel Falcao

29 Man United appearances, 12 Chelsea appearances

After becoming one of the most lethal strikers at the beginning of the 2010s, United fans found themselves in shock when they found that Radamel Falcao would be a deadline day arrival back in 2014. With Angel Di Maria already through the door, many believed the Colombian goalscorer would only help propel the Red Devils to the top of the Premier League.

Four goals and plenty of disappointment later, Falcao cut his legendary locks and, with a sharper appearance, made a move on loan to Chelsea the following year. There, he managed just one goal in 12 games, simply adding to the curse of the number nine shirt at Stamford Bridge.