REAL MADRID endured a Champions League night to forget as they were comfortably beaten 3-1 by Tottenham at Wembley, losing a match in the group stage for the first time since October 2012.
A Dele Alli double and a Christian Eriksen finish following a sweeping counter-attacking move topped off a marvellous performance from the home side and secured their qualification to the knockout stages.
It wasn’t all bad news for Madrid though as Borussia Dortmund could only manage a 1-1 draw with APOEL, leaving the 2016 Champions five points clear of both and all-but guaranteeing Madrid’s progress to the next stage.
Manchester City also qualified for the knockout stages in style as they came from a goal down to beat Serie A leaders Napoli 4-2 in Naples.
Sergio Aguero became the club’s all-time top goalscorer with his 178th goal for the club, and further goals from John Stones, Nicolas Otamendi and Raheem Sterling saw City continue their dominant start to the season.
On a memorable night for Premier league clubs, Liverpool also recorded a 3-0 victory to go top of Group E.
Goals from left the merseysiders have now scored 11 goals in their last three
On Tuesday, Manchester United edged closer to the knockout stage with a 2-0 win over Benfica at Old Trafford.
An own goal from 18-year-old Mile Svilar and a Daley Blind penalty were enough for the home side who maintained their perfect start to the Champions League campaign.
The same cannot be said for Chelsea though, as they lost 3-0 away at Roma.
Stephan El Shaarawy had the home side two up in the opening and a Diego Perotti strike after the break compiled more misery on Antonio Conte and the current Premier League Champions.