Crouch silences San Siro and sets up a thriller back at the Lane

It is supposed to be Milan, seven times winners of the European Cup and royalty when it comes to the Champions League, who break their opponents' hearts in the dying minutes of games but last night it was Tottenham who carried out the classic counter-attack assassination.

This was a famous night for English football's new Champions League team. Some clubs have to wait years to beat Milan at San Siro. Some never do. But Tottenham have done it in their first season in the competition and at times last night they played like the old hands of Europe soaking up the pressure and then running a sword through the Italians on the break.

Milan lost the plot. They lost it in the demented tackle by the former Arsenal midfielder Mathieu Flamini on Vedran Corluka in the second half that put the Croat out of the game. Harry Redknapp called it "a leg-breaker" and he was right. Milan lost the plot in the ruckus at the end of the game when Rino Gattuso butted Joe Jordan, Redknapp's assistant.

Jordan, an ex-Milan player, is no angel when it comes to provocative comments from the touchline but he made a sucker out of Gattuso. The Milan captain and former Rangers man said later they spoke "in Scottish" yet at 33, Gattuso should know better than to try to hit people in front of the cameras.

A hugely effective player in his time, Gattuso's powers are fading now and you could say the same for the likes of Alessandro Nesta and Clarence Seedorf, who tried to prop up Milan last night. Robinho never really got in the game and Zlatan Ibrahimovic showed us only a brief moment of why he is so highly rated in Italy.

Instead, the night belonged to the arrivistes. That was Redknapp's bright young team who, even without Gareth Bale, looked like a side who can play in these great European arenas without any fear. This was the first time that any Spurs team in the history of the club had won away in the European Cup and it was some way to do it.

Redknapp's match-winner, Peter Crouch, took a battering all night from Nesta and Mario Yepes, the Colombian defender who was embarrassed by Aaron Lennon in the build-up to the goal. But bruised and knackered, Crouch was still there when Lennon skipped away from Yepes with 10 minutes left to steer the ball into the Milan goal from just inside the area.

The return leg on 9 March will be unmissable. Milan will be forced to throw everything at Spurs to try to retrieve the deficit. Only once in the history of the Champions League has a side lost in the first leg at home and still won the tie. As for Spurs, with White Hart Lane roaring them on and Bale back in the team it is hard to imagine them being anything other than determined to kill off Milan.

Redknapp is only too happy for his team to play up to their image of cavalier counter-attackers but they know how to defend. There were almighty performances from William Gallas and Michael Dawson last night, the latter launching himself in front of a close-range shot from Robinho in the closing stages.

Behind those two, goalkeeper Heurelho Gomes kept Spurs in contention twice in the second half when he made instinctive saves from two Yepes' headers that looked like they were destined for the net. By the end, Redknapp had thrown on Jonathan Woodgate for his first playing time since November 2009.

There is a great spirit in this Spurs team, that much is obvious from the way in which they stick together in the difficult moments. Redknapp touched on that when he said that Luka Modric had insisted on travelling to Italy even though it is just 13 days since the operation to remove his appendix. Sure enough the Croatian, on as a substitute, was the man who sent Lennon on his way to make the goal.

Spurs' progress in the competition started as a bit of a novelty – something different from the usual four who occupy the Champions League places. But it has become something much more intriguing. They are a good 90 minutes away from being in the quarter-finals and, as has been the case since Redknapp took over, they are outstripping all expectations.

They had the best of the early stages of the first half and there was an unusual series of events in which Milan lost their goalkeeper, Christian Abbiati, to what looked like a case of delayed concussion.

The Italians found Crouch an awkward customer all night and they dealt with him by kicking the England striker as much as possible. Nesta caught him with a crafty high kick at the end of the first half. There were openings for Spurs but nothing that they could build into a clear chance. They only really tested the substitute goalkeeper Marco Amelia in the first half with Rafael van der Vaart's long-distance effort, which was pushed over.

It was after half-time that it started to heat up and it all began with that two-footed lunge by Flamini on Corluka. Not only did he injure his opponent but Flamini turned to exhort the Milan fans in the aftermath as if it was something to be proud of. Van der Vaart tried to tell him how inappropriate his actions were. Flamini apologised to Corluka after the game.

Jordan clashed with Gattuso on the touchline for the first time shortly after that. The Milan player, who has missed the last month with injury, grabbed Jordan round the neck that time. In interviews with Italian television afterwards Gattuso apologised but refused to divulge what it was Jordan had said that had so enraged him.

Milan, who had brought on the Brazilian striker Alexandre Pato for Seedorf at half-time, piled on the pressure but Gomes and Spurs held strong. Then, with 10 minutes left Modric managed to get Lennon away and he isolated Yepes who was unable to turn quick enough as the winger went past him. Crouch was waiting in the box to finish it off.

Late on Ibrahimovic had a spectacular volleyed goal at a corner disallowed for a needless push on Dawson. This was Spurs' night and the chaos that broke loose on the touchline around Gattuso at the final whistle only went to show how much it hurt Milan.

Milan (4-3-1-2): Abbiati (Amelia, 18); Abate, Nesta, Yepes, Antonini; Gattuso, Thiago Silva, Flamini; Seedorf (Pato, h-t); Robinho, Ibrahimovic. Substitutes not used Papastathopoulos, Oddo, Jankulovski, Merkel, Legrottaglie.

Tottenham Hotspur (4-4-2): Gomes; Corluka (Woodgate, 58), Gallas, Dawson, Assou-Ekotto; Lennon, Palacios, Sandro, Pienaar (Kranjcar, 76); Van der Vaart (Modric, 61), Crouch. Substitutes not used Cudicini (gk), Pavlyuchenko, Defoe, Bassong.

Man of the match Crouch.

Match rating 8/10.

Referee S Lannoy (France).

Attendance 80,000.

Man for man marking

Milan

Christian Abbiati

Went off injured before he had the chance to be fully tested by Spurs. 6

Luca Antonini

Repeatedly beaten by the pace of Aaron Lennon in the first half. 4

Alessandro Nesta

Could have conceded a penalty, but improved as the game went on. 5

Mario Yepes

Struggled with Crouch and well beaten by Lennon for the goal. 4

Ignazio Abate

Provided Milan with some much-needed width down the right flank. 6

Mathieu Flamini

Fierce but ought to have been sent off for a dangerous lunge on Corluka. 4

Thiago Silva

Struggled with the promotion from defence to central midfield. 5

Gennaro Gattuso

Typically fiery, allowed himself to be distracted by personal feuds. 4

Clarence Seedorf

Struggled to get into the game and was replaced by Pato at half-time. 4

Robinho

A few clever touches but mainly quiet against a steady defence 5

Zlatan Ibrahimovic

Expertly-shackled by Spurs. Had a late equaliser rightly disallowed. 5

Substitute

Marco Amelia

An early substitute for Abbiati. Could do little for Crouch's goal. 6

Tottenham

Heurelho Gomes

A quiet first-half but made some crucial second half saves at 0-0. 7

Vedran Corluka

A smooth and comfortable display before he went off injured. 6

Michael Dawson

Assured on the deck and in the air, with a heroic stoppage-time block. 8

William Gallas

Deployed his Champions League experience in neutering Milan. 7

Benoît Assou-Ekotto

Characteristically cool on such a big stage. Used the ball smartly. 7

Aaron Lennon

Dangerous running throughout, found Crouch well for Spurs' goal. 8

Sandro

Perfect in the tackle and picked his moments to break forward. 9

Wilson Palacios

Some disciplined defensive work, shutting down any of Milan's space. 8

Steven Pienaar

Preferred to Niko Kranjcar, he was lively and clever down the left. 6

Rafael van der Vaart

Generally quiet but nearly scored with a wonderful chip in the second-half. 6

Peter Crouch

The target for diagonal balls all night, but took his goal neatly. 7

Substitute

Jonathan Woodgate

Did not look like he had been out of the game for as long as he has. 7