Real Madrid's five most expensive January transfers of all time

Cameron Smith

• 18 Jan 2025 15:00 CST
• 4 min read

Real Madrid are the most successful club in European football history and they are responsible for some of the most expensive transfers of all time.

However, Los Blancos have been unusually reserved when it comes to mid-season spending over the years.

Below, FootballTransfers runs through Real Madrid’s five most expensive January transfers of all time.

READ MORE: Real Madrid's 10 most expensive transfers of all time

5. Brahim Diaz - €17m (from Man City, 2019)

Brahim Diaz spent five years at Manchester City, but he wasn’t convinced by his first-team pathway and opted to join Real Madrid for €17m in January 2019.

The Spaniard left Man City with 15 senior appearances under his belt and he was required to spend three seasons on loan at AC Milan before finally breaking into the Real Madrid team.

READ MORE: Real Madrid's 10 biggest sales of all time

4. Lassana Diarra - €20m (from Portsmouth, 2009)

After failing to hit the necessary heights at both Chelsea and Arsenal, Lassana Diarra made a surprise move to Portsmouth in January 2008.

He helped Pompey win the FA Cup just four months after his arrival and Diarra’s form convinced Real Madrid to spend €20m on him in 2009.

The Frenchman played 116 times for the Spanish giants, but he left to join free-spending Russian side Anzhi Makhachkala after three-and-a-half years at the Santiago Bernabeu.

3. Fernando Gago - €20.5m (from Boca Juniors, 2007)

A graduate of the Boca Juniors academy, Fernando Gago left his boyhood club to join Real Madrid for €20.5m in January 2007.

The Argentina midfielder went on to make 121 appearances for Los Blancos, however he struggled for game time under Jose Mourinho due to competition from Sami Khedira and Xabi Alonso.

Gago subsequently joined AS Roma on loan in 2011, before signing a permanent deal with Valencia the following summer.

2. Klaas-Jan Huntelaar - €27m (from Ajax, 2009)

Klaas-Jan Huntelaar spent three prolific years at Ajax and his prowess in the Eredivisie prompted Real Madrid to spend €27m to acquire his services in 2009.

The Netherlands legend netted 158 times in 257 games for Ajax and big things were expected of him when he moved to the Santiago Bernabeu.

But, Huntelaar spent just one season at Real Madrid, scoring eight goals, before he was sold to AC Milan for €15m.

1. Reinier - €30m (from Flamengo, 2020)

Real Madrid’s lack of ground-breaking winter spending is proven by the fact that Reinier is currently their most expensive January signing of all time.

Los Blancos signed the Brazilian when he was just 18 years old, with the club eager to repeat the success stories of Vinicius Junior and Rodrygo.

However, Reinier has failed to justify his price tag and he appears unlikely to ever make the grade at Real Madrid.

Real Madrid’s five most expensive January transfers of all time