John Toshack was sacked by Real Madrid in November 1999 as a consequence of league's bad form following a 3–2 defeat against Rayo Vallecano that left them in eighth position and re-hired Vicente del Bosque who previously 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 2024 this was the last season that Real Madrid went on to finished outside the top four spot in La Liga to date.

Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.