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Tottenham earned a memorable first-leg win at AC Milan to give themselves the upper hand in their last-16 Champions League tie against the Serie A leaders.Peter Crouch stroked in the winner after 80 minutes from a pass by Aaron Lennon, who had led a blistering Spurs counter-attack. Tottenham keeper Heurelho Gomes had twice kept his side level with two superb saves from Mario Yepes headers. Zlatan Ibrahimovic had a late goal disallowed for Milan as Spurs held on. The match was marred by a touchline fracas when Milan's combative midfielder Gennaro Gattuso head butted Tottenham assistant manager Joe Jordan after the final whistle. Gattuso had already been in an altercation with Jordan, seemingly shoving him in the face close to the Spurs dug-out when they clashed during the game and the Italian continued his battle after the match.

The result would not have helped the combustible Italian's temper, in addition to the AC Milan captain picking up a yellow card which rules him out of the return leg, as his side were made to look second best for most of the game at a rain-soaked San Siro.

A touch of nerves from Spurs almost let Milan back into the game but, after Robinho's far-post shot had been diverted wide, Ibrahimovic was rightly punished for pushing Michael Dawson before guiding in a shot with his back to goal. The aim of Tottenham boss Harry Redknapp was to make sure his side were still in the tie going into the return leg at White Hart Lane but his players did so much more.Crouch, who had come on as a late substitute when his former club Liverpool lost to AC Milan in the 2007 Champions League final, had led the line tirelessly before being rewarded with his late goal. It marked a win which came from some of the attacking football Spurs are capable of but also the type of resolute display Redknapp had doubted his team could produce. Spurs' swashbuckling style has made them one of the entertainers of this season's competition but, despite Redknapp vowing to attack, he also had one eye on tempering his side's adventure with vigilance.

The memory of Tottenham being four goals and a man down after 35 minutes when they played Inter Milan at the San Siro in the group stages might have had an influence on his thinking. He preferred the more defensive-minded Steven Pienaar to Niko Kranjcar, who had grabbed two winners in the last two games, on the left of a midfield also including holding players Sandro and Wilson Palacios. However, there was still plenty of threat up front and the visitors were unlucky not to have a penalty when Rafael van der Vaart's cross appeared to be blocked by the arm of Milan centre-back Alessandro Nesta in the opening minutes.

The aerial threat of striker Crouch made life uncomfortable for the Italian league leaders and he almost scored when Vedran Corluka's incisive pass released Lennon, whose cross was intercepted by keeper Christian Abbiati. In diving to palm away Lennon's cross, Abbiati got a knock to the head and had to be replaced by Marco Amelia.Spurs had a degree of control and comfort, while Milan looked lethargic and laboured. A long range Van der Vaart left-foot strike was tipped over by Amelia before the Dutchman produced a sublime chip which went agonisingly wide as Spurs went close. Milan had brought on Alexandre Pato for the ineffectual Clarence Seedorf at the break and, as they began to to carry more of a threat, Spurs keeper Gomes was called into making a crucial save. From Gattuso's dinked cross AC Milan centre-back Yepes guided a header towards the top corner and it took a dive at full stretch for Gomes to palm his effort wide. The home side's increased appetite spilled over into overly aggressive play at times and ex-Arsenal midfielder Mathieu Flamini should have been sent off for a two-footed lunge on Corluka but he somehow escaped with a yellow card.

Jonathan Woodgate, who had not played since November 2009, came on for Corluka as some of Milan's antics started to ruffle Spurs' feathers. It took another crucial save from Gomes to keep his side level as he again kept out a Yepes header from close range. But the visitors stunned the San Siro crowd when Lennon left the AC Milan side in his wake as he stormed upfield and the winger had the composure to slide the ball across to Crouch to slot in for a greatest victory.