Antonio Rudiger remains the most recent player to make the switch from England, finally moving to the Bernabeu last summer after his contract expired at Chelsea.
We’ve taken a look at their 26 signings from the Premier League, who have enjoyed varying levels of success to say the least.
Antonio Rudiger
After letting his contract run down, Rudiger swapped Chelsea for Real Madrid just before Todd Boehly detonated the joint last summer.
The Germany international has made 42 appearances for the Champions League holders, helping guide his new side into yet another European semi-final. One of the best free transfers of recent times.
Eden Hazard
“I have surely had the worst season of my career individually,” is how the Belgian described his disappointingly injury-ravaged debut season in the Spanish capital.
Three years on and he’s struggled to kick on from there, or make any kind of impact at all. A return of seven goals in 75 appearances for Los Blancos has been downright sad to witness for a player who was arguably the best player in the Premier League whilst at Chelsea.
We miss Hazard tearing it up, but it’s beginning to look increasingly unlikely he’ll ever rediscover his best form at the Bernabeu.
Brahim Diaz
One of the more intriguing transfers of 2018, Manchester City clearly rated Diaz, but the hot prospect decided to return to his homeland and swapped the challenge of breaking into Pep Guardiola’s midfield for the challenge of breaking into Zinedine Zidane’s.
After initially appearing that Diaz would be sent out on loan for the second half of 2018-19, the teenager instead found himself being handed a handful of first-team opportunities with Los Blancos, catching the eye with a clever assist against Huesca and excellent goal against Real Sociedad.
He was on the periphery, making the odd appearance here or there, before a three-year loan to AC Milan.
He looks a much better fit at the San Siro for the Champions League semi-finalists, and it looks increasingly unlikely he’ll return to Spain to play any kind of role back at his parent club.
Thibaut Courtois
Real Madrid fans weren’t particularly happy about the idea of replacing Keylor Navas, and Courtois didn’t exactly convince them it was the right move during his first season in Spain.
“There are times when I feel that I am not appreciated enough,” Courtois said in February 2019, but he’s since turned that around with some absolutely blinding performances between the sticks.
Nobody is questioning the decision to sign Courtois now. Arguably the best goalkeeper in world football.
Javier Hernandez
One of five players to make the move on a temporary basis, with United looking to offload the Mexican forward he joined Real on loan in 2014 with the option to buy the following year.
He scored seven La Liga goals in just 858 minutes of action, however, completing the full 90 minutes just five times, with Real unsurprisingly choosing not to take up their option. Chicharito instead joined Bayer Leverkusen before returning to England with West Ham.
One memorable moment did come of Hernandez’s time at Real, with him scoring the winner in the Champions League quarter-final against bitter rivals Atletico.
Gareth Bale
Previously an out-of-favour left-back at Spurs, Bale had transformed into one of the Premier League’s most dangerous wingers, earning a then-world record move to Madrid in 2013.
Bale scored 106 goals in 258 games for Los Blancos, but he didn’t exactly take on the role as main man following the departure of Cristiano Ronaldo and his time at Bernabeu came to an acrimonious end.
Still, a five-time Champions League winner that scored some goals that were important as they were incredible – and over a hundred of them to boot. It’s a shame the nature of his departure ensured he doesn’t get the appreciation he deserves.
Michael Essien
Another loanee, former boss and close ally Jose Mourinho gave Essien’s career a lifeline by taking him to Real Madrid in 2012.
The pair referred to each other as father and son in their joint press conference to announce the move, and Essien played 35 times in a season that saw Real just miss out on any major silverware.
Spells at AC Milan and Panathinaikos followed before the former Chelsea man last turned out for Indonesian club Persib Bandung.
Luka Modric
The six-time Croatian footballer of the year and widely regarded as one of the most underrated footballers in the world, Modric moved from Tottenham to Real for £30million in August 2012.
He has gone on to make over 450 appearances for Los Blancos and finally ended the Ronaldo/Lionel Messi duopoly to win the Ballon d’Or in 2018.
Undoubtedly one of the greatest players in the history of Real Madrid and still producing match-winning performances at the very highest level at the age of 37.
Emmanuel Adebayor
Not one to settle for a quiet career, Adebayor had been told he was no longer part of the plans at Manchester City, signing on loan for Real in January 2011.
He scored eight times in 22 appearances across all competitions, including goals against future loan club Tottenham in the Champions League.
Ricardo Carvalho
“If there was a possibility to sign with Real Madrid, I would go there right now swimming or running,” said Carvalho, after reports emerged that Mourinho was interested in taking him to Real.
Sure enough, two weeks later, the central defender was reunited with his former Chelsea boss, playing 48 times in his first season before dropping down the pecking order, playing just 29 times in two further seasons before joining Monaco and ending up in China.
Cristiano Ronaldo
450 goals in 438 appearances. Yeah, that didn’t turn out too bad.
Xabi Alonso
Spain international joined Real from Liverpool for £30million in 2009, despite not actually wanting to leave Anfield.
He made 236 appearances in just over five years at the Bernabeu, winning La Liga and the Champions League before seeing out the last three years of a stellar career at Bayern Munich.
Alvaro Arbeloa
Right-back Arbeloa returned to his childhood club just three years after leaving, moving from Liverpool for a relatively cheap fee of £5million.
He went on to play 233 times in a white shirt in a seven-year spell at the Bernabeu, before briefly returning to England and then retiring in 2017 after a season at West Ham which yielded just four appearances.
Lassana Diarra
In one of the most up-and-down, bizarre careers going, Diarra had lined up for Chelsea and Arsenal before Real signed him from Harry Redknapp’s Portsmouth in January 2009 – costing them £20million.
He won La Liga and the Copa Del Rey in his three and a half years at Real, before spells at Anzhi Makhachkala, Lokomotiv Moscow, Marseille and Al Jazira, who he left in December 2017 before joining Ligue 1 champions PSG the following month.
Julien Faubert
“His agent should be knighted by the Queen,” commented Paul Merson, after West Ham’s Faubert somehow engineered a loan move to Real in 2009.
He signed for six months with the option to buy, but made just two appearances, missed training when he thought he had a day off and was spotted taking a nap on the bench during a match against Villarreal.
Arjen Robben
“I didn’t want to go, but the club wanted to sell me,” Robben said after his two-year spell at Real came to an end as the club looked to bring in Kaka and Cristiano Ronaldo.
The general consensus is that the club should not have let the former Chelsea winger go in his prime, especially as he went on to cement his legend at Bayern Munich.
Gabriel Heinze
Heinze demanded a move to Liverpool due to a disappointing amount of first-team action at Manchester United, but Sir Alex Ferguson insisted he would not be allowed to sign for their arch-rivals despite giving the defender permission to find a new club.
Both sides ended up bringing in lawyers, and a Premier League arbitration panel eventually concluded that the permission to seek a new club “was unambiguous in that it envisages only an international transfer”.
He spent two years at Real before leaving for Marseille, ending his career at Roma in 2012. His coaching career has ranged from quite promising (Velez Sarsfield) to downright disastrous (Atlanta United). It’ll be interesting to see how his stint at Newell’s Old Boys ends up.
Jerzy Dudek
Famed for his antics in the 2005 Champions League final, Dudek’s extra-time double save from Andriy Shevchenko was in fact voted the greatest Champions League moment of all time.
However, having lost his place in the side to Pepe Reina, Dudek left Anfield in 2007, joining Real on a free transfer. In four years, he played in just two league matches, with Iker Casillas ahead of him in the pecking order.
Ruud Van Nistelrooy
Running away from Cristiano Ronaldo at United, Van Nistelrooy preceded him at Real, joining for €14million in 2006 after hitting 95 goals in 150 Premier League appearances.
He top scored in his first season in La Liga, earning the nickname ‘Van Gol’, only for injuries to hamper the rest of his time at the club – though he did leave with a phenomenal record of 64 goals in 96 appearances.
Jose Antonio Reyes
After three years at Arsenal, Reyes denied reports he was seeking a move to Real a number of times, before Arsene Wenger eventually facilitated the transfer, as Julio Baptista swapped clubs with Reyes, both on season-long loans.
He scored twice off the bench to seal the La Liga title with a comeback win over RCD Mallorca, and did stay in the Spanish capital – joining rivals Atletico for €12million that summer.
Jonathan Woodgate
Despite being bogged down with injuries throughout his 18 months at Newcastle, Real shelled out £13million for Woodgate in 2004 – only for him to be out for another year, making his famously calamitous debut over a year later.
Woodgate scored an own goal and was sent off for two bookable offences on his first outing in a Real shirt, but then impressively managed to nail down a first team spot, being labelled “Madrid’s true leader” in the Spanish press.
Sadly, injuries again hampered his progress, and in July 2007 he was voted by readers of Marca as the worst signing of the 21st century.
Michael Owen
Considering some of the fees Madrid had paid for players (see the £13million they spent on Woodgate), £8million for Owen was a bit of a steal, the forward leaving Anfield with a strike rate better than a goal every other game.
He managed 13 goals in 36 appearances at Real, finishing the season with the best minutes-per-goal in the division, but was shipped out to Newcastle, who forked out double what Los Blancos had paid just a year earlier.
Thomas Gravesen
“I told him to stop joking. Seven days later, it was done.”
Even Thomas Gravesen didn’t believe that Real Madrid were interested in bringing him to the club from Everton in 2005.
Rather than being noticed for his ability, Gravesen was taken note of for his particularly shouty on-field antics, before he was shipped out in 2006 after a training ground bust-up with Robinho.
David Beckham
After appearing set for a move to fierce rivals Barcelona, Real hijacked Beckham’s departure from Manchester United and signed him for €37million.
He couldn’t have joined at a worse time, though, as Real went trophyless in Beckham’s first three years at the club before winning the league on the final day in 2007 ahead of the England hero’s impending departure to LA Galaxy.
Nicolas Anelka
£23million was a heck of a lot of money in 1999, but Real Madrid weren’t afraid to shell out that much on Anelka, who had scored 23 goals in 65 appearances for Arsenal, and later said he never should have left.
Having already made a reputation for being a bit awkward, Anelka managed to fall out with Vicente del Bosque, and spent just one season at Real, managing two La Liga goals before they recouped the money spent as he returned to boyhood club PSG.
Steve McManaman
Only the second-ever Englishman to play for Real Madrid, McManaman joined on a free transfer in 1999 having left Liverpool.
In an excellent first season, he scored a tremendous volley in the 3-0 Champions League final win against Valencia, before slipping down the pecking order – but still winning two La Liga titles and another Champions League prior to his departure in 2003.