Tottenham were knocked out of the Champions League as Juventus came from behind to move into the quarter-finals.
The first leg in Italy ended 2-2 and Son Heung-min put Spurs ahead at Wembley with a scuffed finish from Kieran Trippier’s low cross.
But Gonzalo Higuain scored an equaliser when he steered in Sami Khedira’s pass.
And less than three minutes later, Paulo Dybala raced on to Higuain’s through ball and slotted past Hugo Lloris to seal a 4-3 aggregate victory.
Tottenham came close to scoring an equaliser that would have taken the tie into extra time but the impressive Son shot narrowly wide from 20 yards and Harry Kane headed against the post in the 90th minute.
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For Spurs, who last reached the Champions League quarter-finals in 2010-11, it was a first defeat in 18 matches, while Juventus are unbeaten since 22 November – a run of 20 games.
Mauricio Pochettino’s side are the first English team this season to be eliminated from the Champions League.
Elsewhere on Wednesday, Manchester City lost 2-1 to Basel but gained a 5-2 aggregate win to join Liverpool in the quarter-finals.
Manchester United and Chelsea could make it four Premier League teams in the last eight of Europe’s top club competition when they play the second legs of their ties next week.
United entertain Sevilla on Tuesday following a goalless first leg in Spain, before Chelsea play at Barcelona on Wednesday after it finished 1-1 at Stamford Bridge.
