Real Madrid will rebuild during the 2008/09 off-season with two goals in mind: a third straight league title and a full-fledged assault on the Champions League. The first incorporation of the summer was that of Argentine centre-back Ezequiel Garay, who will play on loan for Racing Santander during the forthcoming season. Rafael Van der Vaart became the second reinforcement after leaving Hamburg and signing for Real Madrid for the next five seasons. The 2008/09 winter transfer brought in Dutch striker Klaas-Jan Huntelaar from Ajax, defensive midfielder Lassana Diarra from Portsmouth and right midfielder Julien Faubert from West Ham United.

The first player to land at Real Madrid's doorstep was Racing Santander centre-back, Ezequiel Garay, who will remain on loan with his former team for one more season. Real Madrid's second acquisition of the summer was Dutch midfielder Rafael van der Vaart, who left Hamburg to sign a five-year contract in Spain. In early December, Klaas-Jan Huntelaar became the first signing of the winter transfer window. The striker was followed by Lassana Diarra, a defensive midfielder who arrived from Portsmouth. The coaching staff also underwent a change and Juande Ramos stepped in as the new head coach. On the final day of the winter transfer window, Real Madrid acquired the services of West Ham United's Julien Faubert.

The first to abandon the Spanish capital was Antonio Cassano. The Italian forward who joined Real Madrid in 2005/06  was transfered to Sampdoria. Javier Balboa and Pablo García exited shortly thereafter; the former who joined Quique Sánchez Flores at Benfica. The last two players to depart Real Madrid were Esteban Granero and Roberto Soldado, both of whom have joined Getafe CF. On Monday 1 September, the final day of the transfer window, Robson da Souza Robinho was transferred to Manchester City.