Tottenham had the first chance of the game when Van der Vaart shot, but it fizzed just wide, but Tottenham marked their intention early, they are out to score and kill this game early. Milan threatened, when Seedorf played in Ibrahimovich from his own half. Ibrahimovich controlled it down with his chest but Dawson poked it out for a corner, But Milan were unable to make anything of the chance. Tottenham again went straight to the attack with Modric pinging the ball across field and then it was crossed over for Crouch who headed it down for Van der Vaart who went for it, but Abbiati gathered the ball. Abbiati stayed down holding his mouth implying Van der Vaart caught him, but he was ok. And whenever Tottenham got the ball, they passed directly to the man forward, always going on the attack and with Modric’s movement there was always space for someone, and the direct style off passing was utilized for Crouch to head it down for Van der Vaart. When on the ball Pato showed his tricky as if it was a reminder that he can do something special, and with Robinho and Ibrahimovich in attack with him, Spurs had to on top form. Also with no Pirlo it was left up to Seedorf to play that deep playmaker role, rarely out of his own half, but when he received the ball would put in dangerous long balls for Milan target man, Ibrahimovich. Flamini would roam the pitch while ex Tottenham player Prince Boateng was much more attacking. Gomes denied Ibrahimovich with 15 minutes gone when Ibrahimovich’s curling free kick was pushed out for a corner, but nothing came from it. Tottenham had a good chance when Pienaar’s cross came in for Crouch but his header wasnt on target and fell wide. Crouch feel folding his header, but no treatment was needed. Spurs so were on the attack again when Van der Vaart shot but it was blocked and went out for a corner. they played it short but it was headed clear for Milan to go on the counter attack but Spurs defended well and cleared ranks with a big clearance up towards Crouch, but he was adjudged to have foul his marker. Prince Boateng won yet another free kick for Milan, which was whipped in by Pato and Gomes came but a miscommunication ment Crouch headed it clear, but Milan were unable to capitalize on the loose ball. Milan had a chance when Thiago passed to Robinho who did brilliantly to control and move into the space in one move, but his shot was far from brilliant as he shot high and wide. A.C Milan came extremely close to scoring when Pato went round the on rushing Gomes and pulled it back, the shot by Robinho was a scuffed effort and went off the back of the sliding defender and was looping in but Gallas was on the line to clear it away and did so well as Robinho was in there charging it don with his leg high also. A great opportunity that really should have been taken. Tottenham showing that they can leak a goal, but still look dangerous. Tottenham were always trying to find a way through, but kept being denied but were gaining free kicks and a lot of corner, but where unable to do anything effective with it. Van der Vaart came close with a free kick, but it was just over, but Abbiati seemed to have it covered if it were on target. As the game progressed Milan seemed to get more fo a foot hold in the game, but for their possession and pinning Tottenham back, the goals had yet to come. And though Lennon and Pienaar where helping at the back, they were doing well to stifle Milan, and it may well be playing into Redknapp’s hands. When Tottenham did go on the attack, there seemed to be move of a gap between Milan’s defense and Midfield and there seemed space for Tottenham to exploit and Vander Vaart again put Abbiati into action saving his long range effort. Nearing the end of the effort Spurs defense seemed to be a bit shaky when the crosses came in. Gallas cleared one, when the only players around him where two of his teammates and Gomes, and then Gomez flapped slight at another. Milan were apply pressure, and Tottenham seemed happy to take it and break on the counter. The half ended 0-0 with Tottenham not looking like scoring, but for all Milan’s possession and apart from one very good chance neither did they.
The second half started much in the same way as the first with an effort for Peter Crouch, but instead of going for goal he headed it back across goal, but no one was there, a good chance went begging. Milan threatened on the attack with Pato dribbling in before playing ion Robinho who gave it to Abate who crossed low but didn’t find anyone. Jankulovski Jankulovski was booked for his sliding tackle on Aaron Lennon, and would have to be careful for the remainder of the game. Corluka and Lennon started to link up more up the field in Milan half and a half chance arose, but apart from shouts for a handball nothing came of it. The hand ball was never a real penalty claim, but still rang out at White Hart Lane. Tottenham went on the attack with Crouch their main target man, but he rose with the assistance of holding down the defender. Lennon started to become a much bigger threat and ran past with ease and delivered a nice cross, but no one was close, but Seedorf controlled it with his thigh but it seemed to hit his hand also, but again no penalty was given. The crowd erupted when Flamini dived in two footed on Assou-Ekotto, not only because of the challenge but because it was Flamini. Through out the game you could tell when he received the ball as he was resoundly booed for it, but he seemed to enjoy it. He was yellow carded for the tackle. Milan had another great chance to score when Gomes through the ball out to Van der Vaart, but Thiago saw the pass and intercepted and put the ball into the Tottenham defense, Abate played in Robinho who shot first time making Gomes make the save, which he did well with one hand, but the ball was loose in the six yard box and he flapped a hand at it. It bounces off Gallas’s foot back off Gomes and as Gallas went to clear it Robinho had nicked it off him and and shot wide. Milan had now missed two good chances in the game to score, and where soon feeling the pressure. Gareth Bale soon came on fo Van Der Vaart who walked down the tunnel and not onto the bench with his team mates, maybe he was assured that he was going to stay on and was frustrated at being subbed, time will tell. Flamini soon made his presence felt to Bale knocking him over. Tottenham started to get some of the possession and Sandro was key to that, whether it was winning the ball or playing it to the free man to keep the ball moving, he was influential to Tottenham’s attacks. Milan came close to scoring when Pato’s shot was hit hard and low, but hit the side netting. it was a nice move in which Merkel was involved. Merkel came on for Prince-Boateng. It was another good chance for Milan, and one Milan needed to score as the game started to move into the last 15 minutes, and much more into Tottenham advantage. Not many would have expected Tottenham not to be on the attack, but they defended well and showed the strength and depth that their team has. Going into the last 10 minutes and Milan got a corner, The ball fell to Ibrahimovich who kept control of the ball well, but Dawson didnt give him an inch to shoot, and in the end laid it off for Pato, but he too didnt have any space and in the end Tottenham got the ball clear to up hold their aggregate lead. Spurs got a corner with five minutes to go, but nothing came of it, but when Bale passed it short to Sandro he ran and won the ball and ran it into the corner where he kept oot there for as long as he could, holding off two players and still keeping control of the ball with little touches. He was Tottenham key man tonight, a real general in midfield. Redknapp did a great bit of business in signing him. Milan tried desperately to get the ball forward and into Tottenham’s box, but any ball that ventured in or near was duly hoofed away. But then Milan worked their way forward, not looking for the long pass, but passing close and dribbling in, and great one touch play Robinho managed to get a shot away but it went out for a corner. A foul in the box gave Tottenham a free kick, which was kicked as far forward as possible. In the end Milan were unable to break down the resilient Tottenham and when the final whistle was blown, White Hart Lane burst into cheers and soon into song. Spurs went through to the next round 1-0 on aggregate, which over the two legs they deserved to do, A great night for the Fans, the Players and the Manager.