Real Madrid's five worst January transfers of all time

Cameron Smith

7 Feb 2025 23:30 CST
2 min read

Real Madrid frequently avoid conducting meaningful transfer business during the January window, but Los Blancos have made exceptions on a number of occasions.

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However, some of their mid-season signings have quickly turned into major flops.

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

Ze Roberto - €9m (from Portuguesa, 1997)

Ze Roberto was the epitome of a journeyman and he spent a small fraction of his playing career at Real Madrid following a €9m move from Portuguesa in January 1997.

However, after playing only 21 games for the club, Roberto returned to Brazil to join Flamengo on loan in 1998 and he subsequently secured a permanent move to Bayer Leverkusen for €7m.

Roberto went on to play for the likes of Bayern Munich, Nacional, Hamburg and Palmeiras before retiring in 2017.

Antonio Cassano - €5.5m (from Roma, 2006)

Antonio Cassano spent four-and-a-half years at AS Roma before his move to Real Madrid in January 2006, but his time in Spain was over extremely quickly.

The Italian made just 29 appearances for Los Blancos, notching four goals during that time, and he was sent on loan to Sampdoria in 2007 after failing to acclimatise to life in La Liga.

The Serie A side opted to make the deal permanent in 2008 and Cassano spent the rest of his career back in Italy.

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

Klaas-Jan Huntelaar arrived at Real Madrid having scored 105 goals in 136 games for Ajax, but his short spell in Spain was certainly not as successful.

The Dutchman joined Los Blancos for €27m, but he played just 20 times for the club, scoring eight goals, before being sold to AC Milan for €15m after only seven months at the Santiago Bernabeu.

Huntelaar then joined Schalke in 2010 and he became a club legend at the Bundesliga side, racking up 128 goals in 249 games.

Lucas Silva - €13m (from Cruzeiro, 2015)

Lucas Silva is one of the biggest transfer flops in Real Madrid’s history.

The Brazilian midfielder moved to the Santiago Bernabeu for €13m in January 2015, following an impressive breakthrough at Cruzeiro, but he only made a total of nine first-team appearances for Los Blancos.

He was loaned to Marseille and back to Cruzeiro during his time in Spain, before leaving Real Madrid on a free transfer in 2019.

Reinier - €30m (from Flamengo, 2020)

Current ETV

Reinier

AM, M (C)

Granada

Reinier

AM, M (C)

Granada

ETV Range

€1.8M - €2.7M

Following the successes of Vinicius Junior and Rodrygo, Real Madrid attempted a transfer repeat with the signing of Flamengo midfielder Reinier in January 2020.

However, the Brazilian has been sent out on loan four times and he is yet to make his senior debut for Los Blancos.