Tottenham Hotspur’s first Champions League adventure saw them meet Italian giants Milan in the last 16.
After topping a group featuring Werder Bremen, Twente and European champions Inter, Spurs were handed one of the toughest draws possible.
Milan would go on to win Serie A in 2010/11, but they met their match in Europe, with newcomers Tottenham eliminating them 1-0 on aggregate.
Harry Redknapp’s side secured an unforgettable win at San Siro. Let’s relive that magical night in Milan…
Tottenham are halfway to reaching the Champions League quarter-finals for the first time in their history having beaten Milan 1-0 at San Siro in the first leg of their last 16 tie.
Harry Redknapp’s men controlled the first half before weathering an onslaught in the second, taking a slender but deserved advantage into the second leg at White Hart Lane.
A first-minute appeal for a Tottenham penalty was waived away when Rafael van der Vaart’s cross was blocked by the arm of Alessandro Nesta, with the visitors’ loud appeals immediately dismissed.
Spurs dominated the opening stages with their steadfast defending and quick transitions, with goalkeeper Christian Abbiati having to be alert to a couple of Peter Crouch shots as well as several teasing crosses.
However, Abbiati’s night was cut short after just 18 minutes when he sustained an injury colliding with Crouch for a high cross. Marco Amelia was brought on in his place.
Milan’s first meaningful foray into the final third saw William Gallas block a cross from Zlatan Ibrahimovic through the six yard box as the hosts’ frustrations in breaking down Spurs continued.
Aaron Lennon’s torment of Mario Yepes and Luca Antonini saw him skip past the duo and deliver a cross of his own through the corridor of uncertainty without a telling touch, before Rafael van der Vaart forced Amelia into his first save with a stinging strike from 18 yards.
After half-time, the Rossoneri were squirming when Van der Vaart managed to swivel away from Thiago Silva and reverse a dink towards goal, though it mercifully for Milan landed the wrong side of the post.
Milan went incredibly close to taking the lead when Gennaro Gattuso’s cross was headed on by Yepes and looked destined for the top corner, only for Heurelho Gomes to throw up a long arm and palm it aside.
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