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Top 5 times Premier League clubs regret signing players from Real Madrid

5 times Premier League clubs regretted breaking the bank to sign players from Real Madrid

Raphael Varane is edging closer to joining Manchester United – and the Red Devils will be hoping their latest raid on Real Madrid pans out better than their previous one.

United, like many of their Premier League rivals, have struggled to get the best out of players signed from Los Blancos despite paying eye-watering fees over the years.

It may be an old adage, but players often seem to struggle to adapt to life in the English top flight, with Rio Ferdinand voicing such concerns over the proposed signing of Varane.

Indeed, there is no shortage of players who have failed to live up to expectations after moving from Real Madrid to the Premier League.

Without further ado, here are five transfers which left clubs regretting their splurges.

Angel Di Maria

Di Maria lasted just one season at Old Trafford before joining PSG
Di Maria lasted just one season at Old Trafford before joining PSG (Image: 2014 Getty Images)

Angel Di Maria is considered one of the finest wingers in Europe, but the less said about his time with Manchester United the better.

The Red Devils paid a British-record £59.7million to sign the Argentine winger from Real Madrid in 2014 but he lasted just one season at Old Trafford.

Di Maria scored four goals in 32 games during a hugely-underwhelming season under Louis van Gaal before departing for Paris Saint-Germain for a fee of £44million, meaning United made a significant loss on the player.

Alvaro Morata

Morata was in the spotlight for his wastefulness in front of goal
Morata was in the spotlight for his wastefulness in front of goal (Image: Getty)

Alvaro Morata has faced fierce criticism wherever he has played, be it for Real Madrid, Juventus or at international level with Spain.

That being said, he has also proved himself to be a classy player capable of stepping up on the big stage, as shown with his three goals at Euro 2020.

But Morata found goals hard to come by after Chelsea signed him for a club-record £60million from Los Blancos in 2017.

The 28-year-old scored just 24 times in 72 games for the Blues before he was shipped out on loan to Atletico Madrid in January 2019.

Fortunately for Chelsea, they managed to recoup the vast sum they spent on Morata when he sealed a permanent return to Atletico last summer.

Robinho

Robinho joined the Sky Blues on deadline day in 2008
Robinho joined the Sky Blues on deadline day in 2008 (Image: Action Images)

Another expensive forward transfer which failed to deliver the goods, Manchester City were left red-faced after signing Robinho for £32.5million on deadline day in 2008.


The Brazilian was supposed to usher in a new era of silverware for City after their takeover by the Abu Dhabi United Group.

But Robinho managed a paltry tally of 16 goals in 53 games before returning to Santos on loan after 18 months, with no trophies in his cabinet from his time at the Etihad.

Danilo

Danilo failed to live up to his £27million price tag at the Etihad
Danilo failed to live up to his £27million price tag at the Etihad (Image: REUTERS)

Sticking with Manchester City, the Sky Blues would have been expecting far more from Danilo after his £27million arrival from Real Madrid in 2017.

The Brazilian showed patches of his quality but failed to nail down a starting role in Pep Guardiola’s side during a time when full-backs were regularly chopped and changed.

Things have worked out rather well for City, however, as they used Danilo as a makeweight in a part-exchange deal to sign Joao Cancelo – one of their standout performers last season – from Juventus in 2019.

Michael Owen

Owen moved to Newcastle for a club-record fee in 2005
Owen moved to Newcastle for a club-record fee in 2005 (Image: PA)

Michael Owen spent just one season at Real Madrid before returning to the Premier League after Newcastle United agreed a club-record £16.8million transfer in 2005.

The Ballon d’Or winner was unveiled in front of a 20,000-strong crowd at St James’ Park, but he failed to bounce back from his mixed spell in Spain on Tyneside.

Owen managed 30 goals in 79 games for the Magpies but his time with the club was notoriously injury-ravaged and he was unable to prevent their relegation from the Premier League in 2009.

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