Real Madrid were handed 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 another to give Spurs a deserved victory at Wembley.
Cristiano Ronaldo scored the lone goal for the holders with his side already down by three.
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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 winning streak against Spurs.
The 32-year-old has scored 10 goals against Tottenham in all competitions, which is more than he’s scored against any other English club.
Tottenham have qualified for the Champions League last 16, while Madrid lost their second consecutive game after defeat at Girona on Sunday. (Goal.com)