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There is no doubt that Real Madrid have had some of the biggest names in football to represent them through the various decades of their history.

Indeed, names such as Cristiano Ronaldo, Raul, Alfredo Di Stefano, Ferenc Puskas, Ronaldo, Roberto Carlos, David Beckham, Sergio Ramos and Iker Casillas are just a handful of men to have donned the famous white jerseys of Los Galacticos in the past – quite frankly, there are far too many players to name that are worthy of recognition.

Due to their star-studded set-ups over the years, bettors have always taken a keen interest in Real Madrid as well, as they are usually found to be one of the favourites in each and every competition that they ever take part in, which makes checking out a must!

However, there have been some times where they have made the odd deal that just simply has not worked out or was strange when it initially took place.

Here are just some of those flops:

Jonathan Woodgate

Jonathan Woodgate’s time at Real Madrid was awful and one that many might have actually forgotten about as it was so bad. The ex-England international had to wait a whole year to make his debut because of injuries and it was a disaster when he eventually made it out on to the pitch.

He scored an own goal and then received a red card against Athletic Club on his debut and things never got going. In fact, in 2007, he was named the club’s worst signing of the 21st century by MARCA readers.

Theo Hernandez

Theo Hernandez took so much time to sign that the left-back needed to hit the ground running quickly. However, the former Atletico Madrid man could not do it at the Santiago Bernabeu.

He made just 13 league appearances for Real Madrid in his first season at the club before being loaned out to Real Sociedad and eventually sold to AC Milan in 2019.

Asier Illarramendi

Arriving as a promising 23-year-old, Real Madrid splashed out 32 million euros on Asier Illarramendi in 2013.

Unfortunately, things did not work out as he failed to make the desired impact and was sent back to Real Sociedad just two years later.

Nuri Sahin

Nuri Sahin was one of Turkey’s most promising prospects at one point, as he had made his senior international debut at just 17-years-old.

In 2011, he joined Real Madrid but failed to impress Jose Mourinho following his 10m euro move and ended up leaving the club permanently three years later after just four La Liga appearances.

Julien Faubert

When thinking of a transfer that makes you scratch your head, Julien Faubert’s move to Real Madrid from West Ham United is certainly one of them.

No-one could quite believe that the Frenchman had managed to bag a temporary switch to Madrid for the second half of the 2008/09 season.

Furthermore, it seemed all the more bazaar as he looked out of his depth at the Santiago Bernabeu immediately and played just two league games.

Javier Saviola

Joining Real Madrid from arch-rivals FC Barcelona is risky business, especially if a move does not work out. Javier Saviola experienced that switch.

The former Argentina international – who was once a truly exciting forward – swapped Blaugrana for Los Blancos but only lasted two seasons as he failed to make the grade.

Royston Drenthe

Royston Drenthe – a football with so much promise that the disappointment he did not fulfil his potential truly hurts.

Real Madrid beat a host of rivals to his signature in 2007 and paid 14m euro, but it was a disaster.

The Dutchman had behavioural issues and just could not get going. He has since had a number of clubs and just never found the feet that initially had him looking like one of the next big stars of the game.

Antonio Cassano

Speaking of behavioural problems, Antonio Cassano has a reputation that preceeds him and things were no different at Real Madrid.

Lasting just a season at the Santiago Bernabeu, the Italian forward fell out with Fabio Capello and was even criticised by president Ramon Calderon for his attitude. Cassano has since admitted he was an idiot, though.