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#3 Tottenham v AC Milan (2010-11)
If Spurs were to face Milan today, there would be no contest that the Premier League side would start as a hot favourite. Rewind seven years, though, and the story was very different.
Tottenham, under the guidance of Harry Redknapp, were just building to become the force they are today. Gareth Bale was starting to emerge as a superstar, aided by a stunning performance against Inter in the group stages, in which Spurs had bettered the defending champions.
There were still questions about their temperament and experience when they went to San Siro for the first leg of their last-16 encounter. Spurs had not played in the European Cup since 1962, when their manager was just 15, and had precious little experience, while in the group stage they had failed to achieve a single away win.
They confounded their critics, then, by winning in Italy, with Aaron Lennon setting up Peter Crouch to score with 10 minutes remaining. More memorable, though, was Redknapp’s assistant Joe Jordan squaring up to Milan hardman Gennaro Gattuso after the game.
Zlatan Ibrahimovic, Pato, Robinho & co. were unable to square the game back at White Hart Lane, despite a siege on the home goal in the first half that saw William Gallas made a crucial clearance off the line.
The adventure that season would not last much longer – Real Madrid easily accounted for them in the quarter-finals – but in many ways, it was just beginning for the club.
