The 1999–2000 season was Real Madrid C.F.'s 69th season in La Liga. This article lists all matches that the club played in the 1999–2000 season, and also shows statistics of the club's players.

Summary

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.

Players

Squad

Transfers

Winter

Reference:

Competitions

Overall

Friendlies

La Liga

Results summary

League table

Results by round

Matches

Copa del Rey

Champions League

First Group stage

Second Group stage

Knockout stage

Final

FIFA Club World Championship

Group stage

Third-place play-off

Squad statistics

Players statistics

Goal scorers