April 23, 2021

Man Utd

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Ronaldo disappointing Fergie to Rooney’s brilliance: Man United and AC Milan

11 min read

Of all the draining nights Old Trafford has hosted over the last 111 years, May 9 1958 must have been one of the most emotional.

Three months and a day after British European Airways Flight 609 crashed on its third attempt at take-off in the slushy snow of Munich, killing eight Manchester United players, United won their European Cup semi-final first leg against AC Milan.

Harry Gregg, Bill Foulkes, Kenny Morgans and Dennis Viollet, all survivors of the Munich wreckage, started and Viollet scored. Callously, the Football Association deprived United of Bobby Charlton, selected in England’s summer tour ahead of the World Cup in Sweden, where he did not play.

Matt Busby, given the last rites in his Munich hospital bed, summoned the strength to attend the FA Cup final defeat by Bolton Wanderers at Wembley but did not travel to Milan, instead listening on the wireless as United were vanquished 4-0 in the return leg and 5-2 on aggregate.

Milan, United’s first opponents post-Munich, bookended Busby’s second European odyssey, for the teams were drawn together at the semi-final stage in 1969 when United were holders. Milan were vanquished by the Real Madrid of Di Stefano and Kopa in the 1958 final in Brussels but hoisted their first European Cup in 1963 at Wembley, the scene of Busby’s zenith in ’68.



Harry Gregg punches the ball clear at Old Trafford against Milan in 1958
Harry Gregg punches the ball clear at Old Trafford against Milan in 1958

“The San Siro in Milan is an intimidating place to play football,” Denis Law recalled of the first leg in ’69. Law found the Italian football anathema during his brief spell with Torino in the early 60s and United’s own conservative approach was compromised by the withdrawal of Nobby Stiles with a locked knee and John Fitzpatrick was expelled for retaliating against Kurt Hamrin. Milan prevailed 2-0.

“Milan played the classic Italian game,” Charlton said. “Rock solid in defence and always looking for breaks. They did maximum damage on two of them.”

The United players already knew Busby, affectionately known as The Old Man by Charlton, was preparing to step upstairs. Wearing their all-white away kit on home turf, Best, Law and Charlton lined up together for the last time in European competition at Old Trafford three weeks later and Charlton lashed in the opener on 70 minutes.

“We laid siege to the Milan defence but the catenaccio -the bolted door of Italian defence – had been slammed back into place,” Charlton colourfully cursed. Law was subjected to the ‘old tricks’ from Milan’s defenders, with his former Torino teammate Roberto Rosato particularly physical. Law warned Rosato repeatedly and eventually knocked his two front teeth out with the referee looking elsewhere. The Milan goalkeeper Fabio Cudicini, the father of former Chelsea custodian Carlo, was hit by a missile lobbed from the Stretford End.

What smarted more than Rosato’s rumbustiousness for Law was he was denied a legitimate goal that would have levelled the tie. Law scrambled the ball over the line yet the French referee dismissed United’s appeals – and the celebrations from the Stretford Enders.



Law and Brain Kidd (right) are convinced its over the line
Law and Brain Kidd (right) are convinced its over the line

The footage from the game – which amounted to a single camera – conclusively captured the ball beyond the Milan goal line. Years later, The Sunday Times reported Milan among the Italian clubs guilty of offering gifts to referees

“Had that goal counted we would have been favourites to reach the final against Ajax,” Law lamented. “Ajax were not the force they were to become in Europe and AC Milan demolished them 4-1 to win the cup.” Busby shook the players’ hands and graciously thanked them for their efforts. United did not play European Cup football for another 24 years.



Busby thanks United fans against Leicester in May 1969
Busby thanks United fans against Leicester in May 1969

Sir Alex Ferguson was 18 years into his epoch by the time United and Milan were paired together again in the Champions League round-of-16 in 2005.

Milan had visited Old Trafford two years earlier in the soporific 2003 final they won against Juventus on a penalty shootout following a goalless 120 minutes, yet Carlo Ancelotti’s holders had somehow surrendered a 4-1 first leg advantage in the quarter-finals in 2004 against Deportivo la Coruna, losing the return leg 4-0 in Galicia.

Milan arrived in Manchester widely regarded as Europe’s outstanding side: the Brazil international Dida in goal, the Seleção’s World Cup-winning captain Cafu at right-back, the peerless Paolo Maldini at left-back and the impregnable pairing of Alessandro Nesta and cult United hero Jaap Stam at centre half. The midfield triumvirate was brimming with silk and steel: Alessandro Pirlo, Clarence Seedorf and Rino Gattuso. Playmakers Kaka and Rui Costa supported the predatory Hernan Crespo, on loan from Chelsea.



Try finding a weakness with this lot
Try finding a weakness with this lot

The mood at United was mutinous amid Malcolm Glazer’s attempts to buy the club and 5,000 fans protested outside Old Trafford ahead of the first leg in February. United had been overwhelmed by Arsenal’s Invincibles the previous season and Jose Mourinho’s Chelsea juggernaut had blown them out of the water.

United’s line-up included Rio Ferdinand, Roy Keane, Paul Scholes, Ryan Giggs, Cristiano Ronaldo and Wayne Rooney, with Ruud van Nistelrooy back from injury via the bench, but it was an ageing side. Keane, Scholes and Giggs were all in their 30s and Keane would not see out the year at the club. Scholes would have to reinvent himself as a more possession-based midfielder and Giggs was never quieter against an Italian side.



A United fan protests against the Glazers before the Milan home game in 2005
A United fan protests against the Glazers before the Milan home game in 2005

Despite the chasm in class, United had gaping chances to breach Milan. Ronaldo, only just 20, embarked on a coruscating counter-attack and pinged the ball to Quinton Fortune, who stumbled as Dida dashed out and prodded the ball wide with the first leg goalless. Scholes put a shot past the post he was expected to place within the goalframe and a rusty Van Nistelrooy was profligate in Milan.

Ultimately, United were undone by ‘keeping errors; from Roy Carroll at Old Trafford when he spilt Seedorf’s straight shot into the path of the pouncing Crespo and Tim Howard in Milan, where he mistimed his dive to pat away Crespo’s header. Ferguson refused to publicly blame Carroll – until he dropped him three days later.



Maldini keep tabs on Ronaldo
Maldini keep tabs on Ronaldo

Champions League elimination was the doomsday scenario for Keane, yet he made an exception for Milan: “There was no shame in going out to a team that had Nesta, Maldini, Pirlo, and Kaka in it.” Ferguson was in awe of them, suggesting Cafu had two hearts and and vowing to retire if Maldini continued ‘for another four or five years’. Maldini hung up his boots four years later.

“We play a lot of European teams on their own grounds and have to tolerate a lot of histrionics,” Ferguson said. “We didn’t get any of that from Milan. They conducted themselves in an impeccable manner. That is what makes them a little bit special.”

Milan were still special two years later when, for the third time, they drew United at the semi-final stage of the European Cup. This time, United were renascent, with Ronaldo and Rooney mature, Scholes and Giggs revitalised and Rio Ferdinand a world-class defender in front of a dependable goalkeeper in the former European Cup winner Edwin van der Sar. United had just eviscerated Roma 7-1 in the quarter-finals, reducing an Italian journalist to tears in the Old Trafford press box.

United were duking it out with Mourinho’s Chelsea for the 2006-07 title whereas Milan had all but written off their domestic season following the calciopoli scandal. Milan were one of five Italian clubs found guilty of match-fixing and were initially docked 15 points, eventually reduced to eight. Juventus, the reigning Italian champions, were relegated to Serie B. The vultures circling overhead in Milan flew to Turin.

Milan kept their prized assets, with Pirlo and Gattuso starters in Italy’s World Cup final win over France the previous year, when Ferguson attempted to sign Gattuso. Kaka had assumed the baton from Ronaldinho as Brazil’s talisman and Seedorf was still pulling strings.

With the Scudetto destined for Inter, AC focused on the Champions League and only won half of their 38 Serie A fixtures.



Giggs has it out with Kaka
Giggs has it out with Kaka

In their domestic trip sandwiched between the United ties at Torino, Milan rested six starters in the return tie. Ferguson had settled on a small squad at United and their run-in had coincided with ‘an injury crisis of major proportions’, as Ferguson put it. Three days before the first leg at Old Trafford, Ferguson claimed he had 12 players fit.

Dong Fangzhuo, Kieran Richardson, Chris Eagles and Kieran Lee were on the United bench against Milan at home and Ferguson resisted a single substitution, even with Ole Gunnar Solskjaer available. Ronaldo, dueling with Kaka for the Ballon d’Or scruffily scored on six minutes but Kaka struck twice before the pause, capitalising on the cumbersome Gabriel Heinze, moved to centre half to offset the absence of Ferdinand and Nemanja Vidic, nursing a broken collarbone.

Scholes elegantly flicked the ball through for Rooney to equalise, a pass the England World Cup winner Alan Ball rhapsodised about in a telephone conversation with his son. Tragically, Ball passed away the next day.

Dubiously, Ancelotti sent on two defenders and had the temerity to hook Gattuso with the scoreline 2-2. Giggs played Rooney in down the right-hand channel and, with Nesta breathing down his neck, Rooney clipped the ball past Dida, stood like a batsman giving away his wicket at the near post with 90 minutes and 22 seconds on the clock.



Rooney is mobbed after his 2007 winner
Rooney is mobbed after his 2007 winner

The roar reached higher decibels than any of the first-half strikes against Roma in the previous round and Ferguson embraced his assistant Carlos Queiroz. Once the crowds had dispersed, the adrenaline had stopped and the dust had settled, reality bit: United had never won at the San Siro before, Milan had two away goals and United were due at Goodison Park – the unkindest of grounds before or after a European trip – at lunchtime on Saturday.

United memorably recovered from 2-0 down to triumph 4-2 at Goodison, while Chelsea simultaneously dropped points at home to Bolton. United’s defining day of the title race had arrived and they held a five-point advantage with three fixtures left. Knackered, they flew to Milan with a patched-up Vidic and half-baked Ferdinand and were wiped 3-0.



Ferguson looks on in vain
Ferguson looks on in vain

Ronaldo, schooled by Maldini two years earlier, was reduced to that novice in the lashing rain and would finish second to Kaka in the Ballon d’Or. “Cristiano had a disappointing night and he knows it,” Ferguson noted. “I expected better. I really expected better.

“They’re still young, still improving, and when you see the professionalism and experience in the Milan side it’s a good indicator of where we want to be.” Milan exorcised the demons of their 2005 final collapse against Liverpool in Istanbul by beating them in the Athens final. United channeled the experience and expertise of Milan to win their third European Cup the following year in Moscow.



Ferdinand and Giggs hold aloft the European Cup in 2008

The San Siro had become a graveyard for United. In six meetings with AC and Inter they had failed to score there, never mind win, against Milan. They finally did both in 2010, with their weakest United side in Milan since Jimmy Murphy managed Busby’s decimated team of survivors, rookies and journeymen in 1958.

The San Siro tie was a humdinger, a modern classic. Milan, a waning force who had failed to qualify for the Champions League in 2008-09, where now coached by Leonardo and the city was painted black and blue by Mourinho’s Inter. David Beckham was on loan from the LA Galaxy for a second year running, a vain attempt to remain relevant ahead of the summer’s World Cup in South Africa.

Ronaldinho was past his peak but Milan danced to his samba beat. His deflected third-minute volley unnerved United, with Ferguson memorably filmed telling Jonny Evans to, ‘F—–g wake up’, until the ball hit the standing leg of Scholes – their first and only scorer in the stadium against Inter in ’99 – and trickled over the line just before the pause.

Rooney was in the form of his life and worthy of mention in the same breath as Ronaldo, now of Real Madrid, and Lionel Messi. His two headers came in a sequence of eight headed goals in nine games. Seedorf’s virtuoso flick reduced United’s lead and Nesta misdirected a glaring header in the dying embers to level.



United fans in Milan, 2010
Fans of Manchester United gather at the Piazza Duomo before the Champions League game between AC Milan and Manchester United on February 16, 2010 in Milan

Three weeks later, Avram and Joel Glazer showed their faces at Old Trafford for the return leg with a mounting protest against the family’s ownership painting the stadium green and gold. The movement had started in late January but a fixture quirk meant United did not play at home in a live televised home game for well over a month. The Milan match was shown on terrestrial channel ITV.

After nine encounters spanning 52 years, United finally shed their inferiority complex against AC Milan in a 4-0 rout, with Rooney scoring twice again – his third brace against Italy’s most decorated club. Ji-sung Park did a number on Pirlo, the memory providing his ghostwriter with an open goal ofliterary license.



United finally neutered Pirlo thanks to Park
United finally neutered Pirlo thanks to Park

“He’s a man without blemish,” Pirlo ‘wrote’ of Ferguson.

“But he ruined that purity just for a moment when it came to me. A fleeting shabbiness came over the legend that night.

“At Milan, he unleashed Ji-sung Park to shadow me. He rushed about at the speed of an electron. He’d fling himself at me, his hands all over my back, trying to intimidate me. He’d look at the ball and not know what it was for… Even though he was a famous player, he consented to being used as a guard dog.”

Beckham, a starter in Milan, was treated to a hello, goodbye with United 3-0 up on 64 minutes. It was one of those crowdpleasing cameos Beckham specialised in in the twilight of his career; pinpoint passes with the tempo relaxed and an audacious attempt that Van der Sar beat away.



Beckham dons a green and gold scarf

More memorable was what happened after the final shrill.

It seems rehearsed now (the Manchester United Supporters’ Trust had supposedly contacted Beckham’s father, Ted, about it): with his lap of honour nearly complete and ‘There’s only one David Beckham’ ringing around the Stretford End, a lone green and gold scarf was thrown onto the saturated turf as Beckham approached the tunnel.

The crowd reacted as though Beckham was about to step up for a free-kick and loudened when he noticed the scarf, grabbed it and draped it around his neck to cheers as loud as those that greeted his whipped set-pieces. It crowned another uproarious Old Trafford evening against Milan, just like in 1958.

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