Tottenham 0 // AC Milan 0 (Tottenham win 1-0 on aggregate)
Spurs were on the back foot for the majority of the first half and had William Gallas to thank for keeping them in the match after he hooked off the line after 25 minutes following an error by Heurelho Gomes.
The home side looked far more at ease in the second period and had chances to score through Rafael van der Vaart and Peter Crouch and although Robinho came close to snatching an away goal for Milan at the death, Spurs' 1-0 win in the San Siro proved to be enough to send them through to the last eight in their first season in Europe's premier club competition.
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Despite Crouch's goal in Milan, Redknapp had urged his team to go on the attack and they obliged, taking only 90 seconds to fashion their first chance, with Van der Vaart toe-poking just wide from 20 yards.
Despite the quick start from Spurs, Milan settled quickly and began to dictate much of the play, with Kevin-Prince Boateng, Robinho, and Clarence Seedorf probing the Spurs defence with searching through-balls.
Gomes saved well from a 25-yard Zlatan Ibrahimovic free-kick and Tottenham almost went 1-0 down on 25 minutes when Gomes needlessly raced out of his goal to challenge Alexandre Pato, but the Brazilian slipped past and fed the ball to Robinho, whose deflected shot was superbly hooked off the line by Gallas.
Van der Vaart curled a 25-yard free-kick just over Christian Abbiati's goal moments later but Milan came storming up the other end soon after, with Pato drawing a good save out of Gomes from eight yards.
Spurs came out for the second half much more confidently with Lennon cruising down the right before crossing to Crouch, who was unmarked at the back post. The England striker opted to head the ball across the box but no one was there and he should have headed goalwards instead.
Milan's best chance arrived when Ignazio Abate released Robinho into the box and he fired low at Gomes. The ball squirmed free to the Brazil striker but the Spurs stopper got a hand to the loose ball and Robinho eventually poked wide.
Pato thought he had put Milan back in the tie when he fired towards goal but his shot rippled into the side netting. The home fans' nerves were frayed when Robinho's deflected shot flew just over after a clever one-two with Ibrahimovic in the 92nd minute but Spurs held on comfortably to take the tie 1-0 on aggregate.