Real Madrid's 3-1 loss to Tottenham at Wembley was its 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 it into the knockout phase.
READ: Alli double seals sensational Spurs' last-16 spot
For the holder, it was its biggest defeat at this stage of the competition since a 2-0 loss to Juventus in November 2008.
It was also its first loss in the group stage since a 2-1 defeat to Borussia Dortmund in October 2012.
ALSO READ: Ronaldo defends Real Madrid form: It's the ending that counts
Zinedine Zidane's side, which lost 2-1 to Girona in LaLiga at the weekend, has now suffered back-to-back defeats in all competitions for the first time since January, when it was beaten by Sevilla in the league and Celta Vigo in the Copa del Rey.
Latest on Sportstar
- Sabalenka makes French Open last eight for first time
- Tsitsipas blasts past Ofner to make French Open quarter-finals
- Duplantis sets new 2023 pole vault best
- Champion Napoli ends season with 2-0 win over bottom side Sampdoria
- Benzema scores on farewell but Real held at home by Bilbao