European champions, Real Madrid suffered their worst Champions League group-stage loss in nine years after falling to Tottenham 3-1 on Wednesday.
Dele Alli scored twice and Christian Eriksen added a third to give Spurs a deserved victory at Wembley, with Cristiano Ronaldo netting a late consolation for the visitors.
The two-goal deficit marked Los Blancos’ biggest defeat in the European competition’s group stage since losing 2-0 against Juventus in November 2008
It was also only the sixth time Ronaldo has scored while his team lost in a Champions League match.
Ronaldo, who played for Manchester United before joining Real Madrid in 2009, entered the night on a 17-match unbeaten run against Spurs.
And though the 32-year-old took his tally to 10 goals against Tottenham in all competitions – more than he’s scored against any other English club – it was not enough for Zinedine Zidane’s side.
Tottenham have now qualified for the Champions League last 16, while Madrid lost their second consecutive game after defeat at Girona on Sunday.