Milan 0-1 Tottenham: Spurs secure shock Champions League win at San Siro in 2011

Tottenham Hotspur's first Champions League adventure saw them meet Italian giants Milan in the last 16.

After topping a group featuring Werder Bremen, Twente and European champions Inter, Spurs were handed one of the toughest draws possible.

Milan would go on to win Serie A in 2010/11, but they met their match in Europe, with newcomers Tottenham eliminating them 1-0 on aggregate.

Harry Redknapp's side secured an unforgettable win at San Siro. Let's relive that magical night in Milan...

Match report

Tottenham are halfway to reaching the Champions League quarter-finals for the first time in their history having beaten Milan 1-0 at San Siro in the first leg of their last 16 tie.

Harry Redknapp's men controlled the first half before weathering an onslaught in the second, taking a slender but deserved advantage into the second leg at White Hart Lane.

A first-minute appeal for a Tottenham penalty was waived away when Rafael van der Vaart's cross was blocked by the arm of Alessandro Nesta, with the visitors' loud appeals immediately dismissed.

Spurs dominated the opening stages with their steadfast defending and quick transitions, with goalkeeper Christian Abbiati having to be alert to a couple of Peter Crouch shots as well as several teasing crosses.

However, Abbiati's night was cut short after just 18 minutes when he sustained an injury colliding with Crouch for a high cross. Marco Amelia was brought on in his place.

Milan's first meaningful foray into the final third saw William Gallas block a cross from Zlatan Ibrahimovic through the six yard box as the hosts' frustrations in breaking down Spurs continued.

Aaron Lennon's torment of Mario Yepes and Luca Antonini saw him skip past the duo and deliver a cross of his own through the corridor of uncertainty without a telling touch, before Rafael van der Vaart forced Amelia into his first save with a stinging strike from 18 yards.

After half-time, the Rossoneri were squirming when Van der Vaart managed to swivel away from Thiago Silva and reverse a dink towards goal, though it mercifully for Milan landed the wrong side of the post.

Milan went incredibly close to taking the lead when Gennaro Gattuso's cross was headed on by Yepes and looked destined for the top corner, only for Heurelho Gomes to throw up a long arm and palm it aside.

Former Arsenal midfielder Mathieu Flamini was lucky to avoid a red card when he went in high and two-footed on Vedran Corluka, escaping with a booking but turning a competitive tie into a feisty one, with Gattuso and Spurs coach Joe Jordan squaring off on the touchline soon after.

Gomes was again on hand to save Tottenham as he again instinctively kept out a Yepes header as Spurs felt the heat of the warming San Siro pressure cooker.

As the game entered the final stages, Tottenham seemed comfortable letting Milan have the ball and trying to hit them on the counter attack instead - a tactical decision which yielded the game's only goal.

With 10 minutes to play, substitutes Niko Kranjcar and Luka Modric won the ball back and quickly sought to release the pacy Lennon, who carried the ball 60 yards - including up and over a sliding challenge from Yepes - before cutting the ball back for Crouch to convert and give Spurs a stunning lead.

Deep into stoppage time, Ibrahimovic thought he had found the latest of equalisers with a superb overhead kick, but the whistle had been blown for a foul by the Swede on Michael Dawson and Spurs secured a hard-earned win.

Milan player ratings

GK: Christian Abbiati - 5/10 - Flapped at crosses before being replaced through injury.

RB: Ignazio Abate - 6/10 - Galloped up the pitch and stretched play but wasn't too much of a tangible threat.

CB: Alessandro Nesta - 6/10 - Past his peak but was largely fine at the back.

CB: Mario Yepes - 3/10 - Missed two key headers and was made a fool by Lennon even prior to the winning goal.

LB: Luca Antonini - 4/10 - Could barely keep up with Lennon.

DM: Thiago Silva - 6/10 - Looked a little uncomfortable playing slightly higher up the pitch but did a half-decent job of breaking up play.

CM: Mathieu Flamini - 4/10 - Should have been sent off. A walking liability to his team.

CM: Gennaro Gattuso - 4/10 - Lost his cool and too should probably have seen red. Did not inspire confidence in the midfield battle.

AM: Clarence Seedorf - 4/10 - Failed to pick the lock before being hooked at half-time.

CF: Robinho - 4/10 - Snuffed out of play easily, even when dropping deep to try and see more of the ball.

CF: Zlatan Ibrahimovic - 4/10 - Was unable to provide a focal point in the way that Crouch was able to for Tottenham.

Substitutes

Marco Amelia (18' for Abbiati) - 5/10 - Made a few saves but nothing spectacular.

Alexandre Pato (46' for Seedorf) - 6/10 - Changed the game with his ingenuity but he needed his co-stars to step up.

Manager

Massimiliano Allegri - 4/10 - Milan's best hopes of a goal were through Spurs wilting under unprecedented pressure, which they did not. Allegri's men created very little and were continually outplayed by their inexperienced opponents.

Tottenham Hotspur player ratings

GK: Heurelho Gomes - 8/10 - Deserving of his clean sheet and kept Tottenham alive with a string of unbelievable saves.

RB: Vedran Corluka - 7/10 - Locked down the right side and provided good support for Lennon before his injury.

CB: Michael Dawson - 7/10 - Guilty of over-committing at times but Milan had trouble consistently finding a route around him.

CB: William Gallas - 8/10 - The calming presence at the back. Switched to right-back after Corluka's injury and still played well.

LB: Benoit Assou-Ekotto - 5/10 - Couldn't quite get it going on the ball. Needed Pienaar's help at both ends.

RM: Aaron Lennon - 9/10 - The man of the hour. Beat Yepes and Antonini time and time again. If anything, Spurs should have utilised that outlet more often.

CM: Wilson Palacios - 8/10 - Probably his best performance for Spurs, going toe-to-toe with Gattuso and Flamini and coming out on top.

CM: Sandro - 9/10 - Phenomenal. Excellently broke up play and distributed it to start Spurs attacks.

LM: Steven Pienaar - 6/10 - Tucked inside to create overloads and helped out Assou-Ekotto at the back.

AM: Rafael van der Vaart - 7/10 - As per could only complete around an hour, but he flittered between the lines and caused headaches for a disjointed Milan.

CF: Peter Crouch - 9/10 - Much like rivals Inter earlier in the season, Milan did not have an answer for Spurs continually launching the ball to Crouch to create chaos. Scored a winning goal that will live long in the memory.

Substitutes

Jonathan Woodgate (59' for Corluka) - 6/10 - Spurs needed to take the sting out of the game after half-time and while Corluka's withdrawal was enforced, Woodgate's experience helped plenty.

Luka Modric (62' for Van der Vaart) - 7/10 - Likewise proved a calm head as the game was threatening to get away from Spurs.

Niko Kranjcar (77' for Pienaar) - 6/10

Manager

Harry Redknapp - 7/10 - Tottenham proved they were more than a team who relies on Gareth Bale. Everyone stepped up and did their job to Redknapp's credit.

Player of the Match - Aaron Lennon

Underrated performances

Much like against Inter earlier in the season, Spurs couldn't afford to carry any passengers in a game of this magnitude. Every player did their job.

Aaron Lennon and Peter Crouch were the standouts, but who else caught the eye?

• There's a video on YouTube called 'The Worst of Heurelho Gomes' which is accompanied by the description 'What a truly dreadful keeper - and I am a Spurs fan'. The Brazilian was known for some clangers, but he would also give you games like this where he looked like Mr Tickle.

• Tottenham only made two signings in the summer of 2010 in preparation for their first Champions League campaign - Rafael van der Vaart was the more memorable one, but picking up William Gallas on a free from rivals Arsenal was a shrewd acquisition. He provided a calm head and quality on Spurs' European run.

• Sandro and Wilson Palacios. Midfield extraordinaires. The game of their lives.

Milan stunned at San Siro

The 2010/11 season proved to be a memorable one for Milan, but only domestically.

They stumbled through a Champions League group featuring Real Madrid, Ajax and Auxerre, only managing to take eight points from six games.

Nevertheless, they were favourites for the visit of Tottenham, not least because new star Gareth Bale was injured, Luka Modric only fit enough to come off the bench and Van der Vaart only ever good for 60 minutes at a time.

However, Milan underestimated Spurs in the first half, often conceding possession in daft areas, failing to close players down. They were better after the break, but couldn't provide enough of a threat to even draw.

Zlatan Ibrahomovic's disallowed overhead kick was the only time he made himself a presence on the pitch and his performance set the tone for the Rossoneri's stuttering stars.

The performance was all the more fascinating considering Massimiliano Allegri would become renowned as a specialist in the Champions League later in his career with Juventus. Getting tactically outwitted by Harry Redknapp was not a good look.

Other tidbits

• Gennaro Gattuso and Joe Jordan going at it is pure Champions League heritage.

• Players such as Gattuso, Clarence Seedorf and Alessandro Nesta playing in this era did not feel right.

• This was probably Gomes' last good performance for Tottenham. He nearly cost his side dearly in the return leg (which will be reviewed on 90min at a later date) and was saved by Gallas. But it was a joy to watch him throw his arms around and claw balls away from goal again.

• Modric coming off the bench had such a calming influence on Spurs and was a prelude into how he would become such a key figure in world football over the next decade.

• Crouch scored seven goals in 10 Champions League games in 2010/11. He grabbed just four in 34 Premier League outings. Strange bloke.