#3 Javier Saviola
The transfer of Javier Saviola shocked the football world when he made the move from Barcelona to bitter rivals Real Madrid.
Unlike Luis Figo and a few others, the Argentine was well past his prime when he joined Los Blancos, and arguably, Perez just wanted to take a dig at the Blaugrana by picking up one of their players.
Saviola had a tough time securing a spot in the Real Madrid starting lineup, as he was kept out by the likes of Ruud van Nistelrooy, Raul, Robinho, Arjen Robben and Gonzalo Higuain. The former Barcelona man was restricted to appearances in Cup and other 'lesser' matches, accruing 28 appearances in his two-season stay.
The Spaniard managed notched up five goals in the whites of Real Madrid before moving to Benfica, where he regained his mojo once again. However, Saviola would have been better off spending these two years elsewhere, as Real Madrid signed a player they had absolutely no need for.
#2 Julien Faubert
Next up, we have the former Hammers full-back, Julien Faubert. While Faubert was a decent player, his loan move to Real Madrid shocked one and all, as he looked like a fish out of water in Madrid's star-studded lineup.
Like most names in this list, Real Madrid went ahead with the Frenchman's loan signing, ignoring his long history with injuries.
Despite being a loan signing, Faubert cost Real Madrid €1.5 million for his 54-minute appearance in six months at the club, failing to make an impression. Faubert never found a consistent spot at Real Madrid, let alone their world-class starting XI, as he was evidently not at the same level as his teammates.
Moreover, Faubert infamously dozed off on the bench in a game against Villarreal and also ended up missing training the next day, as he mistakenly thought he had an off day. Six months later, his loan deal was not extended, and the option to buy was understandably not exercised.
Faubert undoubtedly remains one of Real Madrid's most peculiar signings.
#1 Jonathan Woodgate
Taking pole position in our list is Englishman Jonathan Woodgate, who lasted just one season in the Real Madrid whites. Although Woodgate was considered one of the Premier League's finest defenders, he consistently found himself on the sidelines due to injury.
While that put off some of Europe's top clubs, Real Madrid persisted with Woodgate's signing, who spent a year out injured with a thigh problem.
Despite a medical being the first and foremost condition to signing a new player, Real Madrid's team doctors seemingly failed to detect Woodgate's ongoing injury issues. He was injured at the time of his transfer from Newcastle.
The current AFC Bournemouth manager made just nine La Liga appearances for Los Blancos, doing gross injustice to the €18.3 million Real Madrid shelled out for his services.
Jonathan Woodgate was arguably the worst debutant for Real Madrid, scoring an own goal and getting sent off.