Ranked! Real Madrid’s 22 Premier League signings rated from worst to the very best

David Beckham, Cristiano Ronaldo as well as some more head-scratching buys - Thore Haugstad ranks all of Real Madrid’s Premier League signings over the last 20 years 

Rich and glamorous, Real Madrid have long hunted the best players on the planet, but only in the last two decades have they rummaged the Premier League. Since 1999, the Spanish giants have made 22 signings from England. It's certainly been a mixed bag, from extravagant world-beaters to cult heroes, cheap loanees and hapless flops.

22. Jonathan Woodgate

Initially roared on by an optimistic Bernabeu crowd, Woodgate proceeded to steer a shot into his own net on 24 minutes

Dogged by injuries, Woodgate had only played 37 games in 18 months for Newcastle when Madrid shelled out £13.4m for his services in 2004. He was even injured on the day he signed. Rather than recovering swiftly, he remained sidelined for a year, and only debuted in September 2005.

The worst was yet to come. Initially roared on by an optimistic Bernabeu crowd, Woodgate proceeded to steer a shot into his own net on 24 minutes. He then managed to get sent off for two bookings, capping the mother of all nightmare debuts.

Admirably, he fought his way back into the side, but injuries struck him down again. By August 2006, Madrid’s patience had run out and they loaned him out to Middlesbrough, who later made the deal permanent. In total, Woodgate played 14 games in three years. In a 2007 poll, readers of Spanish sports daily Marca voted him the worst signing of the 21st century.

Verdict: Started horribly, went downhill from there 

21. Nicolas Anelka

He also managed to fall out with the affable Vicente del Bosque, which got him suspended from training

At 20, Anelka had already forged a reputation as a difficult character, but that did not deter Madrid from spending £23m on him in the summer of 1999. The ex-Arsenal striker failed to settle off the pitch, and things did not go much better on it: he didn't score in the league until February.

He also managed to fall out with the affable Vicente del Bosque, which got him suspended from training. After two goals in 19 league games, Madrid moved him on to Paris Saint-Germain. 

Verdict: Not at all worth the trouble

Nicolas Anelka

Anelka was banished by Del Bosque following a bust-up

20. Julian Faubert

The six-month stint would go down in Madrid lore, largely because Faubert was accused of falling asleep on the bench

When you can’t hold down a starting spot at West Ham, the last thing you expect is for Madrid to come in for you. But in January 2009, Juande Ramos needed a back-up winger and duly sanctioned a shock loan deal for the Frenchman. “His agent should be knighted by the Queen,” Paul Merson quipped.   

The six-month stint would go down in Madrid lore, largely because Faubert was accused of falling asleep on the bench in a game against Villarreal. He later denied it, saying he'd just closed his eyes because he was bored (that's all right, then).

Faubert also missed a Sunday training session because he thought he had the day off. “The boy just got confused, nothing more,” Ramos said. Having featured for 52 minutes in total, he soon returned to London, and now plays for Finish side Inter Turku.

Verdict: Comedy gold 

19. Thomas Gravesen

He became more known for his overly rough style and his peculiar ways of shouting and joking on the pitch

In January 2005, Gravesen had six months left on his Everton contract when his agent told him he had been contacted by Madrid. “I told him to stop joking,” Gravesen recalled. “Seven days later, it was done.”

Madrid needed a holding midfielder behind Zinedine Zidane and Luis Figo. Gravesen was used to a more advanced role, but while he did a decent job anyway, he became more known for his overly rough style and his peculiar ways of shouting and joking on the pitch. By far his greatest legacy was the ‘Gravesinha’ – a bizarre move fondly recalled in many a Madrid bar since, in which he feigned a pass by touching the ground with his left knee (which then started to bleed).

Gravesen lasted 18 months. In August 2006, a training-ground bust-up with Robinho saw him sold to Celtic.

Verdict: No hit, but a figure of fun 

18. Lassana Diarra

The defensive midfielder was somehow handed the No.10 shirt

In late 2008, Diarra swapped Portsmouth for Madrid in a £20m deal to replace the injured Mahamadou Diarra. The defensive midfielder, who was somehow handed the No.10 shirt, was in and out of the team before moving to Russian outfit Anzhi in 2012.

Verdict: Overly expensive 

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