Tottenham Hotspur FC will entertain AC Milan on 9 March with the cushion of an aggregate lead after Peter Crouch's goal earned Harry Redknapp's side a first-leg win at San Siro.
The second half had been largely memorable for the acrobatics of Tottenham goalkeeper Heurelho Gomes, who twice denied Mario Yepes. But with the match seemingly destined for a goalless draw, Aaron Lennon raced from his own half, leaving Yepes in his wake, and into the Milan box where he teed up Crouch to sweep the ball in.
On the eve of the contest Redknapp vowed to take the game to Milan and the visitors began strongly, passing the ball around with assurance and looking to exploit the height of Crouch from the flanks. Christian Abbiati was called into action four times in the opening 15 minutes, holding on to shots from Crouch and Rafael van der Vaart and twice beating the lanky striker to the punch after Lennon broke down the right.
Indeed, Abbiati's final intervention resulted in injury to the 33-year-old, who was replaced by Marco Amelia on 18 minutes. Milan, deploying Thiago Silva in central midfield due to injuries, created little in the first half other than Zlatan Ibrahimović's low cross which was destined for Robinho, but anticipated by Gomes, and a wayward free-kick from the subdued Sweden striker on the half-hour. The hosts were grateful to be on terms at half-time after Amelia tipped Van der Vaart's shot over, three minutes before the interval.
Massimiliano Allegri needed to take action and elected to bring Pato on for Clarence Seedorf at the interval yet Tottenham almost took the lead when Van der Vaart turned on the edge of the area and sent a clever reverse chip narrowly wide. The hosts came even closer to breaking the deadlock, Gomes displaying extraordinary athleticism to claw Yepes's goalbound header over the bar on 48 minutes. Now San Siro came alive and the match more intense, while Vedran Ćorluka was carried off following a challenge by Mathieu Flamini.
The much-improved Rossoneri were unrecognisable from the first half, surging forward and winning a succession of corners. One again picked out Yepes on the hour, only for the Colombian international to once more meet his match in the inspired Gomes. Milan continued to press forward, Pato combining well with Flamini, whose shot was blocked by Wilson Palacios.
The Rossoneri threw everything at the visitors but in so doing got caught cold by a lightning counterattack on 80 minutes. Sandro, with an interception, and substitute Luka Modrić, with a poked pass between two defenders, were involved initially but the move was all about Lennon who laid on the winner for Crouch after his rousing run.
In the dying moments Robinho's close-range shot was blocked by Michael Dawson's diving tackle, leaving Milan with it all to do, and without the suspended Gennaro Gattuso, in north London.