One night in Milan: Reminiscing a memorable Tottenham evening

LONDON, ENGLAND - MARCH 09: Sandro (L) of Tottenham clashes with Zlatan Ibrahimovic of Milan during the UEFA Champions League round of 16 second leg match between Tottenham Hotspur and AC Milan at White Hart Lane on March 9, 2011 in London, England. (Photo by Jamie McDonald/Getty Images)
LONDON, ENGLAND - MARCH 09: Sandro (L) of Tottenham clashes with Zlatan Ibrahimovic of Milan during the UEFA Champions League round of 16 second leg match between Tottenham Hotspur and AC Milan at White Hart Lane on March 9, 2011 in London, England. (Photo by Jamie McDonald/Getty Images) /
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From a Gennaro Gattuso head-butt to an exasperated Zlatan Ibrahimovic, Tottenham’s last Champions League tie in Italy, in 2011, was certainly one to remember.

An already eventful month for Spurs will culminate next Tuesday evening as they are serenaded by one football’s most famous anthems in Turin. It is not completely unfamiliar territory for Tottenham, and if you believe in their alchemistic performance against AC Milan seven years ago, you can afford to be optimistic about Tuesday’s encounter.

Massimiliano Allegri, the man who Mauricio Pochettino hopes to outwit next week, occupied the Milan dugout that night. And, similar to Allegri’s current Juventus side, his Milan team sheet was filled with a profusion of talent, albeit with many in the twitlight of their careers.

Going back to 2011

On a misty night in front of 80,000 fans, Ibrahimovic, Clarence Seedorf, Alesandro Nesta, Thiago Silva, Robinho, and of course, Gattuso, all started for the Rosoneri.

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In comparison, Steven Pienaar, Wilson Palacios, and Benoit Assou-Ekotto made up a much less decorated Spurs XI. Gareth Bale, who had already terrorized the San Siro’s other residents, was out with a back injury, while Luka Modric was only fit enough for a place on the bench.

However, emboldened by Harry Rednapp, who vowed his side would ‘have a right go,’ Tottenham played with the competence of Champions League regulars. Heurelho Gomes was rarely troubled in the early goings, with most suspense occurring at the opposite end.

Spurs had strong penalty claims in the first minute waved away after the ball struck Nesta’s arm. While Milan’s keeper, Christian Abbiati, was besot by an industrious Peter Crouch.

Rafael Van der Vaart came close from long range, while Zlatan appealed in vain for a penalty of his own. Overall, it was a much tamer first half than Spurs’ previous visit to the stadium, where they found themselves four down within 35 minutes.

The second half at the San Siro

Tottenham started the second period in similar fashion with Van der Vaart coming agonizingly close with an audacious dink. But the introduction of Brazilian Pato soon brought the home side to life.

Gomes’ right tentacle was at full stretch to push over a powerful Mario Yepes header. And minutes later Gomes was again summoned into action by the head of Yepes; this time denying the Colombian from point blank range.

Spurs weathered the storm and the combustibility of the Italians quickly began to show. A reckless lunge from old foe Mathieu Flamini could well have ended Vedran Corluka’s season, let alone his evening. Showing total disregard for the injured Croatian, Flamini proceeded to rally the crowd, which most definitely succeeded in rousing his captain, Gattuso .

The hotheaded Italian put in heavy challenges on Crouch and Van der Vaart before turning his attention to the Spurs bench, pushing Spurs coach Joe Jordan in the face. Miraculously, the referee’s red card remained in his pocket and 11 Milan players remained on the field.

Glory, glory Tottenham Hotspur

But it still wasn’t enough to stop Spurs. In the 80th minute Aaron Lennon and Crouch combined in a moment that will forever live fondly in the memories of Spurs fans. After picking the ball up well inside his own half, Lennon burst forward leaving Yepes on his rear. He then squared it to Crouch who kept his nerve to stroke it home. Spurs had their precious away goal.

Milan huffed and puffed towards the end. Robinho came close before, right at the death, Zlatan acrobatically volleyed home an equalizer. However, the referee correctly ruled it out citing a push on Michael Dawon, leaving the Milan players (and Italian pundits) in dismay.

The referee blew the final whistle but the drama was far from over. Gattuso, whose yellow card had already ruled him out of the return fixture, fancied round 2 with Joe who was once a Milan player himself.

A topless Gattuso tested the coach’s Italian, exchanging a series colorful local colloquialisms before the feeble but infamous head-butt. The pair were quickly separated, which was fortunate for Milan’s captain judging by Harry’s post match comments:

"“Gattuso obviously hadn’t done his homework… Joe was ready. He’d taken his glasses off at the end of the game.”"

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Prior to the game Harry had claimed ‘the sky was the limit’ for his Tottenham side.

However, in the following round Real Madrid proved to be a step too far, comfortably killing off the tie in the first leg.

Seven years on and Spurs seem a much more balanced squad, and one who have already had the better of Los Blancos. Spurs can take hope from the Rednapp’s side’s victory, but with limitless aspirations of their own they will see no reason why they can’t go all the way this time around.