Primera Division: Strikers, Sleepers and the Beast: Real Madrid’s biggest transfer flops

One fell asleep during a game, one caused off-field antics – Real Madrid have sunk a lot of money.

We look back at the most royal transfer flops.


1999-2000, striker, came from Arsenal for €35m – 33 games, 7 goals, 6 assists.

Anelka has scored three of his seven Real Madrid goals at the Club World Cup, with just two in the league. A training strike and a resulting suspension were particularly memorable. Moved to PSG after a year. Played for Man City, Chelsea and Juventus, among others. Retired in India in 2016.


2004-2005, defender, came from AS Roma for €23m – 40 games, 2 goals, 2 assists.

The Argentinian roughneck was sent off twice during his year in Madrid. Played a lot, but rarely convincingly and had to leave after one season. Switched to Inter for 16 million and took off.


2005 to 2008, midfielder, came from FC Sevilla for 20 million euros – 77 games, 13 goals, 6 assists.

The Brazilian was called “La Bestia” but was usually too harmless in the Los Blancos jersey. Was loaned to Arsenal after a year and sold to Roma in 2008 for 10m. Retired in Cluj in 2019.


2004-2006, defender, came from Newcastle United for €18m – 14 games, 1 goal, 0 assists.

The Englishman “shone” on his debut with an own goal and a dismissal – and actually owed everything afterwards. Of the markvoted the biggest mispurchase of the 21st century by readers.


2008 to 2010, midfielder, came from Hamburger SV for 15.5 million euros – 73 games, 12 goals, 11 assists.

Played a good second half of the season in his first Real season, then became a bench press and was retired. In 2010 it went to Tottenham for 10 million euros, in 2018 professional football was over.


2007 to 2012, midfielder, came from Feyenoord Rotterdam for 14 million euros – 65 games, 4 goals, 5 assists.

Came as the talent of the century and nephew of Edgar Davids. In the end he was nothing more than David’s nephew. Appeared in a supporting role as a drug dealer in the hit Dutch streaming series ‘Mocro Maffia’. Now in the lowlands of Spanish amateur football, Drenthe signed on with Racing Mérida in the summer of 2022.


2000-2003, forward, came from Racing Santander for €10.5m – 81 games, 5 goals, 11 assists.

Munitis never settled in Madrid, after two meager years he was loaned back to Santander. Later still active for Deportivo La Coruna and Santander again. Was employed as a coach at the Spanish third division club CE Sabadell until the summer of 2022.


2004-2005, striker, came from Liverpool for 12 million euros – 45 games, 16 goals, 4 assists.

Owen wasn’t a huge disappointment, but he didn’t live up to the high expectations either. After just one season in Madrid, he moved to Newcastle. Retired from Stoke City in 2013.


2006-2007, forward, came from AS Roma for €5.5m – 29 games, 4 goals, 3 assists.

“I did everything to ruin myself,” Cassano said of his real time, which was characterized by escapades. Kicked out of the squad several times for lack of discipline. Joined Sampdoria Genoa in 2007 for €5m. In 2017 he ended his career after several stations in Italy.


2011 to 2012, midfielder, came from Borussia Dortmund for 10 million euros – 10 games, 1 goal, 1 assist.

Sahin conceded one million euros per game at Real – a dubious business. He scored his only goal in the cup against Ponferradina. Was loaned out to Liverpool and then returned to BVB. Coach at Antalyaspor since October 2021.


From 2011 to 2012, midfielder, came on a free transfer from FC Bayern – 12 games, 1 goal, 0 assists.

Altintop did not cost Real a fee, but received a four-year contract. After just one season without highlights, he was sold to Galatasaray. Ended his career in Darmstadt in 2018.


2009, defender, came on a €1.5m loan from West Ham United – 2 games, 0 goals, 0 assists.

To this day, no one knows why Real loaned the French. Played a total of 51 minutes and fell asleep on the bench during a game against Villarreal. Retired in 2019 in the 4th French league.


1999-2000, forward, came from Fenerbahce for €21m – 19 games, 1 goal, 1 assist.

The Bosnian played well at Fenerbahce and Real got into the box properly. But nothing broke with the Madrilenians and was awarded twice. Then kicked at several Turkish clubs.


2012-2013, midfielder, came on loan from Chelsea – 35 games, 2 goals, 1 assist.

José Mourinho thought it would be a good idea to bring Essien to Real. The Ghanaian then actually played often, but mostly extremely mixed. After all, financially it was not a disaster for Real. The loan ended after a year. Retired in 2020 in Azerbaijan.


1997, midfielder, came from Portuguesca for €9m – 23 games, 1 goal, 2 assists.

Choosing Real as the first stop in Europe wasn’t such a good idea after all. Zé Roberto just couldn’t find his way at Los Blancos. Then moved to Leverkusen and really took off.

In 2002, Bayern paid 9.5 million euros. After stints in Uruguay and Brazil, he returned to Germany in 2009 with HSV. Retired at Palmeiras in 2017 at the tender age of 43.

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