"I think the fans are already dreaming. What we've achieved is an impossible dream. Nobody could have seen this coming."
Rarely has a goalless draw elicited a eulogy as glowing, but Harry Redknapp’s post-match precis is as warranted as it is poetic. The gregarious darling of the English game is presiding over the re-invention of Tottenham Hotspur, releasing the shackles and instilling football’s most coveted intangible: an identity.
After his most glorious night in management, he sits in the bowels of White Hart Lane, sporting a pristine black suit and navy tie, charming the assembled media with his off-the-cuff quips.
And as he hails the club’s most impressive European achievement since the UEFA Cup win of 1984, a wry smile creeps across the effusive east Londoner’s face.
Arms folded, leaning towards the podium microphone, he shrugs his shoulders and declares that he will be celebrating with a bacon sandwich, a cup of tea and a walk of his dogs along the Dorset coast.
The classic adage that teams play in the image of their manager rings true with Redknapp’s Spurs. His squad of unlikely heroes, stymied by over-coaching in the past, are flourishing.
Attack, attack, attack
It’s Valentine’s Day 2011 and in the Sala Stampa, the Giuseppe Meazza – or San Siro’s – press room, a 150 square-metre asymmetric area lined with turquoise foldaway chairs, Redknapp is in the mood for romance. On the eve of Tottenham’s first knockout game in the European Cup since 1962, their commander-in-chief is eager to remind those gathered that his troops won’t die wondering.
His side have won widespread plaudits for their commitment to free-flowing, attacking football. They are the joint highest scorers in the Champions League, having rattled home 18 goals in the group stages, and Redknapp is unwilling to temper a key tenet of their success, regardless of the calibre of opposition.
“I have a problem setting up a team that is designed to defend,” he says. “We have not got the players to come here and shut up shop. We are an attacking team and that is how I like it. Attacking football is what got us here in the first place.
"We have had a go all through this competition so we will have a right go again at San Siro. We can score here. We know that. I will tell them to just believe in themselves and what got us here. We’ve got a real chance here. Champions League football is another level. It’s what you dream about.”
It’s a valiant, possibly cavalier declaration of intent as seven-time European champions AC Milan lie in wait. But Redknapp’s philosophy is diametrically opposed to that of his predecessor Juande Ramos, who he replaced in October 2008 with Spurs floundering at the foot of the Premier League table with just two points from their opening eight games.
From humble beginnings, he guided Spurs to the Premier League’s top four in his first full season, securing a maiden Champions League campaign for the club. Now he is hell-bent on grabbing the opportunity to dine at Europe’s top table with both hands.
But in many regards, Redknapp is a victim of his own success. His legendary man-management and preference for signing trusted lieutenants over players recommended by new-fangled scouting technologies lead to accusations of tactical ineptitude.
The suggestion is that he is a manager more likely to tell his teams to ‘go out and play’ than overload them with strategic nuance. Yet the truth is that Spurs are riding a perfect storm created by Redknapp’s effortlessly savvy blend of personality, intuition and experience.
Rafael van der Vaart, a dramatic £8m deadline day signing from Real Madrid the previous summer, is perhaps the chief beneficiary of the Redknapp effect. The mercurial 28-year-old’s talent is not in doubt but he occasionally proved temperamental and disruptive at his previous clubs, as well as on international duty with Holland.
But having lurched in and out of favour during two topsy-turvy seasons at the Bernabeu – including a spell without a squad number ahead of the latter campaign – the playmaker is thriving on the freedom afforded to him by Redknapp, who has built the team around him.
“Harry is a very special man, that’s why I already feel at home at Spurs. It feels like I’m back on the street,” Van der Vaart explains.
“There are no long and boring speeches about tactics, like I was used to at Real Madrid. There is a clipboard in our dressing room but Harry doesn’t write anything on it. It’s not that we do nothing – but it’s close to that.”
Another man to profit spectacularly from Redknapp’s tutelage is a 21-year-old by the name of Gareth Bale, who helps to draw the battle lines for Tottenham’s impending Italian job four months earlier at the same venue against Milan’s cross-city rivals Internazionale.
For so long an understudy to eccentric Cameroonian left-back Benoit Assou-Ekotto, Bale burst on to the scene in the second half of the 2009/10 season, scoring winners against Arsenal and Chelsea. A shuffling of the pack after Assou-Ekotto’s return to fitness sees Bale move forward to left wing – and it proves a seamless transition.
He assists all four goals as Spurs thump Young Boys 4-0 to reach the Champions League group stage, but it is in the historic surroundings of the San Siro where the flying Welshman truly announces himself to the world.
It is a defeat that feels like a victory. Tottenham find themselves 4-0 down after 35 minutes, caught cold by the defending champions, hopelessly out of their depth against Europe’s elite.
But Bale, the purest expression of Redknapp’s free-flowing vision, explodes in the second half, ‘salvaging’ a 4-3 defeat with an astonishing quick-fire hat-trick.
The match takes on further iconic status among Spurs supporters as they beat Inter 3-1 at White Hart Lane four weeks later courtesy of another Bale masterclass. Once again he torments Maicon, one of the world’s most celebrated right-backs – “making asphalt” of him, according to esteemed Italian newspaper Gazzetta dello Sport.
Bale exhibits an intoxicating concoction of pace and raw power in the cauldron atmosphere of White Hart Lane, producing two magical assists for Peter Crouch and Roman Pavlyuchenko. Luis Figo, former Fifa world player of the year and Inter ambassador, tells Redknapp at full-time: “He's just amazing, amazing. He killed us twice.”
But now there’s a devastating sting in the tail. Redknapp’s bullishness as Spurs return to the San Siro offsets the deflation he must feel about confronting the one selection headache he has been fearing the most. He confirms Bale has succumbed to a nagging back injury and is ruled out. “Gareth is a big loss to us with his ability to run the ball and attack people running the length of the pitch, turning defence into attack,” he admits.
So in the month Tottenham-born Adele tops the album charts with 21, an 11-track exploration of anguish and forgiveness, Redknapp leaves Spurs fans nursing broken hearts of their own. There will be no third Milanese “killing” by Bale. Redknapp, the arch-improviser, must look elsewhere for heroes if he is to orchestrate another glory, glory European night for this proud old club.
The dynasty and the dictator
Tottenham’s date with destiny coincides with the Arab Spring, a series of anti-government demonstrations and insurrections across the Middle East borne from poverty, corruption and human rights violations. Some 1,730 miles south-east of Milan in the Libyan port city of Benghazi, protests break out against Muammar Gaddafi’s regime, marking the beginning of the Libyan Civil War.
The parallel between the immediate challenge facing Redknapp and his troops - overthrowing a dynasty and a dictator – feels curiously striking. Hours before kick-off, the sordid underbelly of the Italian game, predicated on the conflation of politics and football, rears its ugly head.
Silvio Berlusconi, Italian prime minister and controversial owner of AC Milan, learns that he faces trial on charges of sexual misconduct. The populist leader and media tycoon has overseen the Rossoneri with an iron fist since his acquisition of the club on 24 March 1986.
He is eventually sentenced for extortion and child prostitution - and later exonerated on appeal - but Berlusconi’s fall from grace is in stark contrast to the rise and rise of Milan under their inscrutable overlord.
His vision upon arrival was to turn the Rossoneri into a superpower, a major player among Europe’s elite. His method was at odds with Juventus’ catenaccio philosophy of the time – a style with a strong emphasis on defence. He favoured an attacking approach, one that would improve fortunes on the pitch and in the boardroom.
The landmark arrival of Dutch duo Ruud Gullit and Marco van Basten in 1987 under former shoe salesman Arrigo Sacchi - who steered Milan to back-to-back European Cups in 1989 and 1990 - was an early declaration of intent. Since then, Fabio Capello, Carlo Ancelotti and Massimiliano Allegri have all assumed the mantle as Berlusconi’s commander-in-chief.
Milan would go on to win 29 trophies during his tenure, including five European Cups. But it is almost four years since the most recent of that quintet - the revenge mission against Liverpool in the 2007 final after their infamous collapse in Istanbul two years earlier.
And in truth, Milan are in a state of flux that can be traced all the way back to that cathartic victory in the ancient surroundings of Athens.
Ancelotti eventually departed for Chelsea in the summer of 2009 alongside 2007 Ballon d’Or winner Kaka, who rejected the opportunity to spearhead Manchester City’s revolution under Sheikh Mansour to join Real Madrid.
Paolo Maldini and Cafu are retired, while Filippo Inzaghi, man of the match at the Olympic Stadium in Greece, is struggling with injury as his illustrious career comes to an end. World Cup winner Alessandro Nesta still marshals the ageing defence, but his best days are widely considered to be behind him.
Allegri is the man tasked with picking up the pieces from previous incumbent Leonardo’s botched stint in the 2009-10 season, when a third-placed finish in Serie A was not enough for the Brazilian to keep his job. His appointment is polarising given his lack of distinction as a player and relative inexperience as a manager, but he ultimately leads the club to the Scudetto – their first since 2004 - at the first time of asking. The feat holds extra weight as it ends a run of five successive Serie A titles by bitter rivals and Champions League holders Inter.
He also displays his steel in dealing with the departure of Ronaldinho just weeks before the Tottenham clash, despite Berlusconi’s public declarations that the flamboyant Brazilian is "the best footballer of all time".
The former Cagliari boss makes it his mission to renew a team that has grown old and stale, and ahead of the visit of Redknapp’s men, the sleeping giants are showing signs of life.
They sit top of Serie A, are safely through to the semi-finals of the Coppa Italia and approach the visit of Spurs in buoyant mood after thumping Parma 4-0 at the weekend courtesy of an inspired display by Robinho. Allegri, 43, even joins in a seven-a-side match at Milan’s training facility, Milanello, on the Sunday before the game.
Domestic form aside, Milan must feel the Champions League draw has smiled on them after finishing in second place in their group behind European behemoths Real Madrid.
Two goals in as many minutes from Cristiano Ronaldo and Mesut Ozil condemned Milan to a 2-0 defeat at the Bernabéu and they could only draw with Europe’s most successful export on their own patch. Tottenham, meanwhile, earnt their top seeding by winning their section ahead of Milan’s co-tenants Inter, Twente and Werder Bremen.
Despite Bale’s injury, Allegri remains wary of his side’s next opponents. "Tottenham have done well without Bale in recent games," he says. "They are an intense, very organised team with a good collective, with individuals who are technically very good. It's the last 16 of the Champions League. It will be very difficult."
He also knowingly plays to Berlusconi’s agenda as he underlines that European glory is top of his to-do list. "We have been top [of Serie A] for 13 games and it's normal that we have spoken more about the league because recently we haven't played in the Champions League," he adds.
“Now instead the Champions League is back and it's always a primary motivation for the club. Seeing that in recent years Milan have gone out in the last 16, we need to give everything to go as far as possible.”
With many of the class of 2007 coming to the end of the road, Milan’s re-invention centres on their new-look forward trio: Robinho, Zlatan Ibrahimovic and Alexandre Pato. Mercurial inside forward Robinho and maverick Ibrahimovic arrived at the San Siro the previous summer, paving the way for last season’s top scorer, Marco Borriello, to move to Roma on loan.
Ibrahimovic claims to have turned down a move to the Premier League and Manchester City in favour of a loan switch to the San Siro because football is not about “playing for the money”. The Swede has played for Italy’s three biggest clubs as well as Barcelona in the past six years but may be reluctant to move to the Premier League after witnessing Robinho’s uninspiring spell with City.
Pato, a relative veteran in Milan, would have one of his best goalscoring returns alongside the pair in the 2010/11 campaign, scoring 16 goals in 33 appearances. Gazzetta dello Sport labels the Tottenham match "Pato’s moment".
“The Spurs defence is not reckoned to be playing very well,” an editorial reads. “AC Milan, with the physical presence of Ibra[himovic] and the speed of Pato, must take advantage of this as the return match in the cauldron of White Hart Lane will not be easy.”
Allegri has also reinforced his squad with the captures of Antonio Cassano, Mark van Bommel and Urby Emanuelson, although all three are cup-tied for the meeting with Tottenham. However, he hasn’t re-invented the wheel just yet. Massimo Ambrosini (33), Inzaghi (37), Marek Jankulovski (33), Nesta (34), Andrea Pirlo (31) and Clarence Seedorf (34) are all out of contract in the summer.
For all that, Allegri has negotiated a transitional period in Milan’s history with distinction, reining in Inter and refreshing a squad that has grown old together. A dynasty that had been threatening to crumble after losing so many of its lynchpins is now reinforced by a fresh face and new ideas.
But Milan being Milan, the wide-eyed Italian is acutely aware that Berlusconi, an integral player in the European Cup’s rebranding as the Champions League in 1992, won’t stand for domestic success alone.
A time for San heroes
The driving rain shows no signs of relenting in ‘The Drinkable City’ – so called because of the 500 fresh water drinking fountains adorning its walls. But the deluge isn’t enough to dampen the spirits of Tottenham’s leader.
Michael Dawson admits that he’s “pinching himself” at the prospect of a Champions League away day at AC Milan. “I love every minute of it,” he declares in the lead-up to the tie. The England international, fresh from a 2-1 friendly triumph over Denmark with the Three Lions in Copenhagen, is making up for lost time after missing out on Spurs’ last trip to the San Siro with a knee injury.
With minutes remaining until a new chapter is written in the club’s storied history, he leads his troops through a confined San Siro tunnel and greets an awestruck mascot. Clutching her hand in his right and a furled pennant in his left, his steely gaze breaks momentarily to glance over his left shoulder.
Milan, hardened by the deceitfulness often required to succeed in European competition and skippered by the cantankerous Gennaro Gattuso, are master exponents of the dark arts. They keep Tottenham waiting in the tunnel for 46 long seconds before finally emerging to line up against their green-tracksuited adversaries.
Compatriots Robinho and Heurelho Gomes, and former Arsenal teammates Mathieu Flamini and William Gallas, embrace, but Dawson is unmoved by the faux pleasantries. He is squarely focused on the daunting task at hand.
Dawson marches Tottenham out into the cauldron of the San Siro but the personnel following him into battle raise eyebrows among the 4,700 travelling supporters.
Kranjcar, a favourite of Redknapp’s who has deputised so well for Bale, is the surprise omission from Tottenham’s starting line-up, with versatile South African midfielder Steven Pienaar preferred in the flying Welshman’s usual position on the left wing.
“Picking Steven Pienaar ahead of Nico Kranjcar was a difficult one, but I just thought Steven had better defensive qualities than Nico – I think he can do a bit more on the other side for us, but Nico will certainly get on at some point,” says Redknapp, who is also without the injured Ledley King and suspended Jermaine Jenas.
Future Ballon d’Or winner Luka Modric’s lack of match fitness costs him a start, but the Croat makes the substitutes' bench after having his appendix removed a few weeks ago. Van der Vaart is given a free rein behind lone striker Peter Crouch, despite earlier concerns about his fitness.
Sandro and Wilson Palacios, disrupters-in-chief in the middle of park, are tasked with stymieing one of the finest footballers of his generation and elegance personified in Seedorf.
Two particularly familiar faces to Spurs fans in Robinho and Flamini are named in Milan’s starting XI. The Rossoneri look set to line up in an unconventional 4-3-1-2 formation, with Gattuso and the former Arsenal man playing either side of Brazilian Thiago Silva in midfield.
Milan’s formidable forward pairing of Robinho and Ibrahimovic – a little and large combination straight out of Redknapp’s playbook – provide a stern examination for Dawson and Gallas at the heart of Tottenham’s defence.
The players disperse after the pre-match formalities with the exception of Dawson and Gattuso, who shake hands and exchange pennants. Dawson wins the toss and the Northallerton-born defender issues his finals words of counsel in a pre-match huddle seconds before French referee Stephane Lannoy begins proceedings.
The intrepid visitors, ostensibly unfazed by the weight of history in the opening stages, impose themselves on the game instantly. Eleven days after prime minister David Cameron criticised “state multiculturalism” in his first major speech on radicalisation and the causes of terrorism, Spurs demonstrate their own cohesive collective identity in spades.
Neat interplay between Pienaar and Van der Vaart down the left flank produces a glorious opportunity for the ‘Bofana Bofana’ international after he latches on to a perfectly weighted backheel from the gifted Dutchman.
Pienaar swipes a left-footed cross from the corner of the 18-yard box in the direction of Crouch and the ball seems to strike Nesta’s trailing arm. The move breaks down but 60 seconds into the tie, Milan know they are in a dogfight.
Spurs have the courage of their convictions to adopt their customary expressive style, but contrary to Redknapp’s pre-match war cry, they’re content to sit deep when their hosts are in possession.
As Redknapp himself would admit in his autobiography Always Managing three years later: “This battle-plan certainly wasn’t going to be gung-ho – in fact, it couldn’t have been more different to our previous visit.”
Three minutes into Spurs’ first foray into Champions League knockout football, 6ft 7in Crouch is learning the hard way that European referees’ interpretation of a foul is wildly different to that of their Premier League counterparts.
The ball is lofted into the corridor of uncertainty by Assou-Ekotto. Crouch contests the high ball with wily Colombian centre-half Mario Yepes and goalkeeper Christian Abbiati, but the Englishman is adjudged to have committed an infringement, presumably because he looks the most obvious perpetrator.
Crouch, such an obdurate focal point, is an uncomfortable presence in the final third of the pitch for Milan’s experienced centre-half duo and he quickly makes a nuisance of himself under the high ball once again. A relatively innocuous tussle with Abbiati in the 16th minute results in the Italian stopper’s substitution. Despite not seeming to hit his head, a worrying delayed reaction means the keeper is stretchered off and replaced by Marco Amelia.
Spurs continue to look assured in possession and confident of keeping their illustrious hosts at arm’s length when they relinquish the ball, but the Rossoneri are threatening to convert moments of individual brilliance into gilt-edged chances. The fleet-footed Robinho dances between the lines before sliding a defence-splitting pass through to Ibrahimovic, only for the Swede to be ruled offside.
A burst of pace from the unmistakable front man minutes later is stopped by a strong challenge by the ubiquitous Sandro. Howls of derision meet the referee’s decision to wave play on. Making his debut in the Champions League, Sandro is justifying his selection in the centre of midfield by setting a ferocious tempo, harrying Gattuso and Flamini, stopping the production line at source.
Palacios, the immovable object signed from Wigan Athletic in January 2009, is more withdrawn than his Brazilian counterpart, but no less effective. He stops the combustible Flamini in his tracks with consummate ease eight minutes before half-time after the Frenchman drives from just inside the Milan half, in turn starving the isolated Seedorf of meaningful possession in between Tottenham’s defence and midfield.
Resolute in defence and inventive on the break, Spurs find further success down the right flank through Aaron Lennon, whose turn of pace is striking fear into the befuddled Luca Antonini.
Not for the first time in the opening period, he squares the Italian up before dropping his left shoulder and knocking the ball towards the byline. The burst is enough to allow him to clip a floated cross into the penalty area, but his delivery lets him down with Crouch primed to pounce in the six-yard box.
With the game ebbing and flowing in the dying moments of the first period, Tottenham’s superiority in the middle third of the pitch pays dividends again as Van der Vaart picks the ball up 30 yards out before forcing Amelia to tip a rasping effort over the bar.
A sodden Redknapp, flanked by trusty sidekick Kevin Bond, continues to bark instructions from the edge of his technical area. Their steely exteriors surely disguise huge internal satisfaction with how their side are performing thus far.
Referee Lannoy brings an end to Tottenham’s first-ever half of Champions League knockout football and the biggest compliment that can be paid to the Lilywhites is that they don’t look out of place at Europe’s top table.
Fanning the flames
Just minutes after hip hop recording artist Plan B scoops the best male solo artist gong back home at the Brit Awards, Allegri unveils his own alternative strategy. Pato replaces Seedorf, who has been stalked out of the contest by the voyeurs in the middle of Tottenham’s midfield.
The Brazilian lines up alongside Ibrahimovic, with Robinho dropping into the trequartista position. The visitors, presumably given their instructions without the use of a tactics board – Redknapp would later reveal he “couldn't even fill a team sheet in” – re-emerge for the final 45 minutes unchanged.
Spurs construct a beautiful spell of sustained possession in the hosts’ half, picking up where they left off before the interval. Van der Vaart latches on to a skewed Lennon cross on the edge of the penalty box with his back to goal, shifts the ball on to his favoured left foot and attempts to catch Amelia out with a delicate chip. The Italian is beaten all ends up but the former Hamburg man’s instinctive effort spins agonisingly past the post.
Minutes later, a wounded Milan, humbled in large parts by their fearless guests, produce a moment of quality. The second of successive corners falls to Gattuso on the edge of the penalty area after a bungled clearance from Assou-Ekotto and the Italian enforcer clips a speculative ball into the congested 18-yard box. Centre-half Yepes latches on to the cross and directs a bullet header towards the top corner, only to be denied by the sprawling Gomes, who claws the ball away from danger with a brilliant one-handed save.
Mindful of Milan’s growing threat, a scornful Redknapp takes a swig of an unbranded isotonic sports drink and roars an expletive-laden order towards his captain before watching Van der Vaart fire a free-kick from 35 yards into Amelia’s arms.
Several phases of play later, Milan’s contempt for Tottenham’s enterprise is laid bare.
Flamini, who can scarcely antagonise Tottenham fans any more after spending four years with Arsenal, lunges in recklessly on right-back Vedran Corluka. The terrible two-footed challenge, later described by Redknapp as “quite scandalous” and “a leg-breaking tackle”, ends the Croat’s night. Referee Lannoy, incredibly, only sees fit to caution Flamini, who is castigated by an incensed Van der Vaart.
As the languid full-back receives treatment, several Milan players, orchestrated by Antonini and Robinho, complain that he hasn’t been taken off the pitch and is therefore delaying the resumption of play. Corluka is stretchered off as Jonathan Woodgate prepares to return to competitive action for the first time since November 2009 after 15 months out with a groin injury,.
Milan take advantage as Woodgate frantically primes himself for action. They spread the play to the right channel before Thiago Silva is scythed down by Assou-Ekotto.
The referee is crowded by five Milan players, but Gattuso’s ire is centred on Tottenham’s assistant manager, Joe Jordan. The inveterate hard man from North Lanarkshire in Scotland, who made 53 appearances for Milan between 1981 and 1983 after signing from Manchester United, looks unfazed despite being throttled by the tempestuous Calabrian.
Redknapp’s number two carved out a fearsome reputation during an eight-year playing spell with Leeds under the uncompromising Don Revie and was once famed for his missing front teeth. This isn’t Jordan’s first rodeo since retiring from playing, either. He’s already been involved in touchline bust-ups with Roy Hodgson, Paul Ince and Newcastle coach Andy Woodman during his time at Tottenham.
“I wasn’t going to move, put it that way. Definitely not,” the Scot would later reveal in an interview with the Daily Mail. Jordan and Gattuso angrily exchange views before focus returns to the action on the pitch – for now.
Milan’s resurgence continues as Yepes brings another good save out of Gomes with a header from point-blank range that would surely have found the back of the net if it had been put a foot either side of the goalkeeper. With his side under pressure, Redknapp shuffles his pack, replacing the excellent Van der Vaart with the slightly more defensively minded Modric for the final third of the game.
A second half that promised so much after a frenetic opening ten minutes is in danger of fizzling out amid assorted breaks in play from tactical fouls and substitutions.
Gattuso picks up a long-overdue yellow card for going through the back of Pienaar, ruling him out of the return leg at White Hart Lane. He is so disgusted at the decision that he refuses to even recognise the referee as he strops his way back to the halfway line.
Can’t smile without you
Seconds after Pienaar’s clash with Gattuso, the South African is substituted. He walks past the crocked Corluka, who hobbles back to the Spurs bench with the aid of crutches, and is replaced by Kranjcar. The home side’s pressure is incessant but not penetrating. They are camped inside the Spurs half but can’t unlock a resolute defensive unit.
Then it happens.
Ibrahimovic picks up the ball 35 yards from goal but his attempted pass into Pato is intercepted by Sandro. The Brazilian feeds Modric, who releases the rapid Lennon.
He bursts into Milan’s half, drives towards the penalty area and skips past Yepes’ despairing lunge. He then draws Nesta before crossing to Crouch and the big man makes no mistake, sweeping the ball into the bottom left-hand corner of Amelia’s goal from the penalty spot with a composed right-footed finish.
It’s a poignant tale of redemption for Crouch, a member of the Liverpool squad beaten by Milan in the Athens final. He endured a torrid time under Rafa Benitez at Liverpool, taking 1,229 minutes to register his first goal for the club and never fully winning over the former Inter boss, who only afforded him 12 minutes in the final. Fernando Torres was brought to Anfield in the summer of 2007 and Crouch found game time even more limited. He returned to Portsmouth the following summer before signing for Spurs in a £10 million deal in July 2009.
Crouch can boast a brilliant England record, having racked up 22 goals in 42 caps. He even has a World Cup goal to his name – against Trinidad & Tobago in 2006. But this strike must surely be among his sweetest.
Tottenham dictate possession after taking the lead, looking more and more like hardened European veterans. Modric, hardly resembling a player who undertook surgery for acute appendicitis days earlier, is pulling the strings from the centre of the park.
With minutes remaining, Ibrahimovic, who has done little to disabuse critics of the notion that he is a flat-track bully, lashes an effort from outside the penalty box high and wide.
In the third and final minute of stoppage time, Milan go close to snatching an equaliser. Ibrahimovic nods Ignacio Abate’s cross back across the face of goal, only for Gallas and Dawson to leave the ball for each other, presenting Robinho with a glorious opportunity to score.
Dawson, mercifully, recovers to deflect the shot out for a corner. From the set-piece, there’s a gut-wrenching moment of despair for Spurs as Ibrahimovic fires the ball into the back of Gomes’ net with a spectacular overhead kick.
He wheels away as the San Siro erupts. But the celebrations are swiftly brought to a halt as the referee penalises the Swede for a push on Dawson as he is jostling for position.
Seconds later, with Crouch in possession in Milan’s half, referee Lannoy blows for full-time, drawing the curtain on a magical night in Spurs’ history. They leave with a priceless away goal and the satisfaction of beating one of the great names in European football – and all without their most prized asset.
The words ‘Can’t smile without you’ – the title of a Barry Manilow song adopted as Tottenham’s unofficial anthem – adorn one of the visiting supporters’ banners high up in the gods at the San Siro as they start wild celebrations that are set to run long into the Milanese evening.
Homework - and home comforts
Milan’s players remonstrate with the officials - but a topless Gattuso has unfinished business to attend to. He marches over to Jordan, picking up where he left off in the second half, and plants his head on the Scot before he is swarmed by players and officials from both sides.
“Gattuso had a flare-up with Joe and obviously he hadn't done his homework," Redknapp jokes after the game.
Redknapp would later write of the incident in Always Managing: “He’s a quiet man, Joe, but anyone who knows him will tell you he’s not the type to mess about. He’s fit as a fiddle and strong, and I think he was about to introduce Gattuso to a Glasgow kiss – and not the type he’d get from his missus (Gattuso is married to a Scottish woman) – when they were pulled apart.”
"Everyone saw the pictures and the history of Joe Jordan and what he was as a player…we knew it was in him because every now and again he’d flare up a little bit," Jenas recalls.
"But he had so much more control over it, I think, as a coach. He's a top, top guy. It was unfortunate that happened because he played for AC Milan. You would have thought Gattuso would have a little more respect for him - but football throws up these heated situations sometimes."
Commenting on TV in his role as an analyst, Graeme Souness remarks that the Italian wouldn’t last five minutes in a locked room with Jordan. Gattuso is eventually given a four-game ban for his actions and admits that he was “nervous” during the altercation with the 59-year-old.
The flashpoint, though, cannot take the shine off the landmark success for Spurs.
"It was a great night, a fantastic performance,” says Redknapp. "They did exactly what we asked of them. We got a great result, exactly what we deserved.”
"It was a great game of football,” adds match-winner Crouch. “I thought we deserved the win in the end. I thought we limited them to not many chances and I think we were the better side. It's a fantastic achievement.”
Nevertheless, Redknapp is also keen to temper his side’s obvious euphoria with realism in his post-match comments. “We've done half the job. We know they're dangerous. We have the advantage but it's half-time. It's still all to play for,” he says.
Tougher tests lie ahead, including a second leg against a wounded Milan in three weeks. But Tottenham’s performance is proof not only that they belong at the very top level, but that they deserve to be regarded as genuine contenders.
The impossible dream
So resolute in the face of Milan’s array of attacking talent, Tottenham are quickly brought back down to earth in a frenetic fortnight that sees them ship six goals against Blackpool and Wolverhampton Wanderers in the Premier League before the return meeting with the Rossoneri. They are humbled 3-1 at Bloomfield Road despite creating a host of gilt-edged chances before surrendering a lead at Molineux in the dying minutes to draw 3-3 with Mick McCarthy's men.
Redknapp also decides to take his players on a short break to Dubai to help recharge their batteries, but his fears over the prospect of Bale missing the second leg with Milan are quickly laid bare - in front of the whole squad.
Jenas takes up the story.
"Before the second leg, we go to Dubai on a trip," he recalls.
"The lads are saying: 'Can we go out for a bite to eat? Can we chill together?' And Harry's like: 'No, you’re not doing anything - we’re training.'
"It's day one and we're training really, really hard. He’s running us a lot and it’s boiling hot. We're about to play a training game... and then Gaz tweaks his quad.
"We’ve gone out there for warm weather training to come back fit and flying. But as soon as Gaz tweaks his quad, Harry just says: 'Right, that’s it - we’re not training.' Calls it off, basically.
"It was only a little bit of tightness - Gaz just felt something and didn't like it - but because it was Gaz, Harry was just like: 'Down tools, everyone. Rest.'
"So that was our preparation for the second leg!"
Mercifully for Redknapp, the scare over Bale eventually proves a minor one as the Welshman is passed fit for the second leg.
Of more concern to Tottenham is the form of Milan, who win three consecutive matches after the first leg, warming up for the trip to White Hart Lane with an impressive 1-0 victory over rivals Juventus in Turin that extends their lead at the top of Serie A to eight points.
With much of the build-up focusing on the hostile reception awaiting Flamini on his return to north London, Redknapp’s insistence that his side won’t rest on their laurels and look to protect their slender advantage is unwavering.
“If we change our style of play I think it would be difficult to say ‘we’ve got a 1-0 lead let’s not give anything away’,” he says. “I wouldn’t want to put a negative thought in the players’ minds at all. We’re at home, it’s a game we want to win. Let’s get after them.”
White Hart Lane is expectant, but the Italians quickly set about forcing Spurs on to the back foot and lay siege to their goal in the first half, aided in no small part by a virtuoso display from the ageless Seedorf.
The hosts improve in the second period, but Allegri’s men, inspired by the familiar theatre of European competition, continue to dictate terms, with Flamini and Pato spurning glorious chances to force extra-time. With the clock ticking down, Robinho once again goes agonisingly close to levelling the scores with a fizzing drive from outside the area.
The final seconds ebb away and referee Frank de Bleeckere’s full-time whistle is met with rapturous jubilation among the sell-out crowd. The game may not have panned out exactly to Redknapp’s liking, but he doesn’t care: a 0-0 stalemate is enough to seal Spurs’ passage through to the last eight.
"We knew we weren’t going to lose," recalls Jenas, who entered the fray as a second-half substitute.
"Having gone to the San Siro and got a result against Inter then obviously getting that result against AC Milan away... at home we were just so confident at that point. We knew we were going to beat them."
Redknapp is now the first English manager to take a Premier League side to the quarter-finals of the Champions League. The victory is made all the sweeter by bitter rivals Arsenal’s elimination from the competition at the hands of eventual champions Barcelona the night before.
"I don't know how far we can go but we've done very well to make the last eight," says Redknapp. "If you'd have said that two years ago, people would have said you were crazy. It's a fantastic achievement and we deserve to be here.
"We won our group featuring the defending champions and we've kept two clean sheets against AC Milan. I think the fans are already dreaming. What we've achieved is an impossible dream. Nobody could have seen this coming.”
Asked how he plans to celebrate, Redknapp provides a typically colourful response. "I'll just have a bacon sandwich, a cup of tea and take my dogs out," he says.
"I've had ups and downs, life is a roller-coaster and I try not to get too down or go overboard. It's about the fans. It was a great night for them.”
Over and out
A quarter-final tie against Real Madrid further captures the imagination but it ultimately proves a step too far for Tottenham.
Jose Mourinho’s men capitalise on Crouch’s 15th-minute red card in the first leg at the Bernabéu, condemning the visitors to a 4-0 drubbing. Further salt is rubbed in Spurs' wounds as former Gunners striker Emmanuel Adebayor effectively puts the tie to bed by helping himself to two of the four goals, with Angel di Maria and Ronaldo also getting in on the act.
The Spanish giants round off an emphatic triumph at White Hart Lane when Gomes fumbles a speculative Ronaldo effort into his own net. Tottenham’s European adventure is over but Redknapp emerges from the memorable white-knuckle ride with his reputation enhanced.
The media continue to eat out of the palm of his hand and there is a concerted campaign to position him as the ideal candidate for English football management’s holy grail – or poisoned chalice, depending on your persuasion – the national team job. Instead, West Bromwich Albion manager Roy Hodgson is entrusted with the position, succeeding Fabio Capello in May 2012, leaving people’s champion Redknapp in the lurch.
Not long after the painful FA snub, his tenure at Tottenham ends in a cloud of acrimony. An increasingly fractious relationship with chairman Daniel Levy, a tax evasion case and the hullabaloo that accompanies his obvious and understandable interest in the England job are all contributing factors.
And so the curtain comes down on a rollercoaster four-year stay at White Hart Lane, but Redknapp’s legacy is assured. He has presided over some of the most attractive football played in the Premier League era. Yet in many ways, that night in Milan is a microcosm of his reign.
A night when his side exhibited their collective spirit in droves. A night when they refused to betray their principles in the face of a superpower. A night when they allowed their supporters, so starved of success, to dream the impossible dream.