Real Madrid are currently assessing the possibility of dipping their toes in the winter transfer market. Kepa is a target and could arrive but Real Madrid have had varied success when they did recruit players in January. They have signed 16 players midway through the season in the past and while some of them have been good, the failures sometimes tend to be easier to recall.
The current second captain of Real Madrid arrived in January from Fluminese during the 2006/2007 campaign. He cost €6.5 million as was brought in as a replacement for Roberto Carlos, who welcomed him to the club and mentored him as he slowly eased out his compatriot. Since then, Marcelo has been the number one left-back at the club regardless of who was on the sideline as manager.
The Argentine striker arrived the same year as Marcelo but had far more competition for a place in the team with Raúl, van Nistlerooy, Cassano and Baptista all in the squad. This signing was a bet Real Madrid had made for the future. He would eventually come good with 121 goals in six seasons in white before he swapped Madrid for Naples. During his spell, 'Pipita', won three leagues, a Copa del Rey and two Spanish Super Cups.
In December of 2008, Real Madrid made the signing of Portsmouth's Lass Diarra official. The French midfielder fought with Mahamadou Diarra and Gago for minutes before the signings of Xabi Alonso, Mesut Ozil and Sami Khedira meant his time on the field would be limited. He would go on to play 116 times in white before moving to Anzhi Makhachkala in Russia.
The Dutch striker arrived in the Spanish captial in January 2009 to cover for the injured Ruud van Nistlerooy. He played in 20 games and score eight goals during his brief stint in place of his compatriot. The summer of 2009 was one of great change at Real Madrid and Huntelaar was sent to AC Milan where he also failed to win over his bosses before a move to Schalke where he really settled and performed excellently.
The Togolese striker only played for half a season with Real Madrid but maintains a great rapport with the fans. The footballer blames his brother for not renewing with the club. "He sent a letter on behalf of my family asking that the club not sign me. I am not saying it was the only reason that they didn't sign me but it did have an effect," he said. He played 22 times and scored eight goals.
At the end of 2014, Jose Mourinho started his crusade against Iker Casillas, who he would sell at the end of the season before his decline had fully set in. The Portuguese asked for the signing of Diego Lopez to replace Casillas and create competition. He would eventually move to AC Milan before returning to Spain to play with Espanyol.
The arrival of Christian Karembeu in 1997 also brought two Champions League. Barcelona were also interested in signing the World Cup winner but Real Madrid won in the end but delayed the signing until the winter market. He spent three seasons at the club before moving to Middlesbrough.
The rest of Real Madrid's winter signings
In addition to these seven, Real Madrid would also sign other players with a little less luck. In the winter transfer market of 1996/97, los Blancos first signed a player over Christmas. Lorenzo Sanz would sign three players in total: Ze Roberto and Christian Panucci before Savio arrived in the winter of 1997.
They did not return to the winter transfer market until 2004 when they brought in Thomas Gravesen. The player was remembered for his personality than what he did on the field. Cicinho and Antonio Cassano followed and Gago arrived along with Marcelo and Higuaín but failed to reach the level many expected him to. Julien Faubert played just 54 minutes in the white jersey and Lucas Silva, the last player to arrive in January on loan at Cruzeiro and looking for more minutes.