John Toshack was sacked by Real Madrid on 17 November 1999 as a consequence of league's bad form even after a 3–2 victory against
Rayo Vallecano which they were trailing 2–0 during halftime and could only turn the game around through a spectacular second half that left them in eighth position. Real Madrid re-hired their legendary defensive midfielder in the 1970s
Vicente del Bosque who previously only managed the club in 1994 and 1996 as a caretaker only. This season marked the start of the Del Bosque era of trophy winning at the club, having taken over from Toshack early in the campaign. The squad was also largely different from the previous squad, with the arrival of
Steve McManaman (
Liverpool) and
Nicolas Anelka (
Arsenal) from the
English Premier League respectively, as well as local talents
Míchel Salgado and
Iván Helguera, to support the budding young talent of
Raúl,
Iker Casillas,
Fernando Morientes, and
Guti, as well as veterans such as
Fernando Hierro and
Roberto Carlos. As of 2025 this was the last season in which Real Madrid finished outside the top four in
La Liga. ==Players==