Real Madrid's 3-1 loss to Tottenham at Wembley was their heaviest Champions League group-stage defeat in nine years.
Two goals from Dele Alli and a Christian Eriksen strike secured a famous win for Spurs and sent them into the knockout phase.
For the holders, it was their biggest defeat at this stage of the competiton since a 2-0 loss to Juventus in November 2008.
It was also their first loss in the group stage since a 2-1 defeat to Borussia Dortmund in October 2012.
1 - Tottenham's 3-1 victory was Real Madrid's biggest loss in a CL group game since November 2008, losing 2-0 against Juventus. Slump. pic.twitter.com/HCn5kihCWQ-- OptaJoe (@OptaJoe) November 1, 2017
Zinedine Zidane's side, who lost 2-1 to Girona in LaLiga at the weekend, have now suffered back-to-back defeats in all competitions for the first time since January, when they were beaten by Sevilla in the league and Celta Vigo in the Copa del Rey..