Real Madrid Transfers: The 5 Best and Worst of the Last 20 Years

Over the years, Real Madrid have used the power of money and the lure of their magnificent history to attract players to the Santiago Bernabeu.

It’s likely most players would admit to having a desire to join such a prestigious name in the world of football.

Many have done so; some have gone on to become legends of the game, but, for others, things did not work out.

This article will look at the five best and worst transfers the club has made over the last two decades.

The Best Five: 1. Zinedine Zidane (2001)

Pride of place goes to the commanding king of football Zinedine Zidane. Madrid paid Juventus a then-world record fee of €52 million for the French ace—arguably the club’s best transfer in the last 20 years.

Zidane had it all and he sat on the throne at Madrid.

His crowning moment came in the 2002 Champions League final against Bayer Leverkusen when a spectacular volley helped Madrid win Europe’s most coveted prize.

Zidane will always be synonymous with greatness, not just at Madrid, but in football. 

2. Cristiano Ronaldo (2009)

What can you buy with €94 million? A country? The presidency? Madrid decided to buy Cristiano Ronaldo from Manchester United—a decision that has largely paid off.

The Portuguese winger has been nothing short of sensational during his time at the Bernabeu.

So far he has won a Spanish Super Cup, a La Liga title and a Copa del Rey, and plenty expect more to come if he stays in Madrid. Made in Portugal, raised in England, finished in Spain. 

3. Luis Figo (2000)

The Portuguese winger’s move from rivals Barcelona was greeted with a pig’s head upon his return to the Camp Nou in the Clasico.

The prank failed to silence Luis Figo; instead it sparked him into life as he achieved high status in Madrid.

Figo had the whole world in his hands alongside his fellow Galacticos, and it wasn’t long before he won two La Liga titles and a Champions League alongside Zidane in a Madrid side that became an emblem of football of the last decade. 

4. Ronaldo (2002)

After suffering a number of injury-ravaged campaigns at Inter, Ronaldo tried to revitalise his career by moving to Madrid and getting back to grips with successful football.

The move paid off as he was soon lean, fit and back to his best, bamboozling defences with power and pace.

His hat-trick against Manchester United at Old Trafford in the Champions League during the 2002/03 season will never be forgotten. Ronaldo was unstoppable when at his best—it’s no wonder he will be remembered as "El Fenomeno."

5. Roberto Carlos (1996)

The Brazilian left-back left Inter after reports at the time claimed he was being used out of position as a winger. However, he soon found his place at Madrid.

During his time there, he made the left-back position his own and became a vital part of the glue that held it all together in defence for over 10 years.

He had pace, power and a cannon in his left foot. His shooting from range and swerving free-kicks terrified goalkeepers around the world. Roberto Carlos was one of the best defenders of all time. He left Madrid in 2007 for Fenerbahce. 

The Worst Five: 1. Jonathan Woodgate (2004)

Despite struggling with injuries at Leeds United and Newcastle United, Real Madrid decided to push forward with a £13.4 million offer for the defender in 2004.

However, the Spanish giants had to wait over a year before they could see the former England international in action.

Jonathan Woodgate's debut included an own goal, but he was spared embarrassment as his side won the game. His luck never changed, and after further injuries, he joined Middlesbrough.

2. Elvir Baljic (1999)

Elvir Baljic arrived in Madrid on the back of an expensive transfer from Turkish side Fenerbahce, but he failed to assume the power and control that was demanded of him from the supporters in the Bernabeu.

The Bosnian failed to live up to the €18 million fee the club spent, making just 11 appearances for the club and only scoring one goal in La Liga.

Madrid sold him to Turkish club Galatasaray, who loaned him out to Fenerbahce and subsequently back to Spanish club Rayo Vallecano.

3. Nicolas Anelka (1999)

After winning the Premier League with Arsenal, Nicolas Anelka was keen on leaving North London for Madrid. At the time, he was nicknamed "Le Sulk" for the way his transfer saga at the Gunners was drawn out.

Things didn’t change much at Madrid. After his £23 million move to Madrid, the Frenchman failed to turn all the promise into a successful career in La Liga, and he was sold to Paris Saint-Germain just a year later. 

4. Antonio Cassano (2006)

The Italy international, often described by many as "enfant terrible" for his attitude on and off the pitch, joined Madrid from Serie A club Roma in 2006.

Under Fabio Capello at Madrid, Cassano struggled to have an impact, and he left Spanish soil to join Sampdoria in 2008.

Plenty of expectation, but it was ultimately excess baggage that proved his less-than-perfect start to life in Spain.

5. Walter Samuel (2004)

Many believe Real Madrid showed knowledge, taste and intellect when they gave Roma €25 million for the Argentine.

At the time, Walter Samuel was ranked among some of Europe’s best defenders, but the newcomer failed to flourish.

His influence and power failed to spread at Madrid, and he was poor during the one season he spent in Spain.

He was sold to Italian giants Inter in 2005 where he has enjoyed an abundance of success—most notably a treble-winning season in 2010 under Jose Mourinho.