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With this season's last-16 having thrown up two Anglo-Italian ties, Goal.com looks back at the best encounters between clubs from these two great footballing nations

SPECIAL
By Mark Doyle

When the draw for the round of 16 of this season's Champions League was made back in December, two ties stood out above all others. They were, of course, the two Anglo-Italian affairs: AC Milan against Arsenal, and Napoli versus Chelsea.

Both promise to be fascinating fixtures, not just because of the undoubted quality of the four participants but also because games involving England and Italy's finest have a tendency to be memorable.

Indeed, as Goal.com has outlined below in chronological order, there has never been any shortage of drama when clubs from these two proud footballing nations have met through the years.

1. JUVENTUS 2-3 MANCHESTER UNITED
1998-99


That Roy Keane’s relationship with Sir Alex Ferguson became so dysfunctional the pair were reduced to trading insults with one another through the media is lamentable. The Irishman, for all his many flaws, remains one of the greatest midfielders ever to have played for the club – one which they have still yet to adequately replace – and arguably his finest hour came against Juventus during the treble-winning campaign of 1999.

Having only managed a 1-1 draw in the first leg of their semi-final tie with the Bianconeri thanks to an injury-time goal from Ryan Giggs, United appeared dead buried after just 11 minutes of the return meeting in Turin, with Filippo Inzaghi having notched twice for the Italian champions.

However, when the going gets tough, the tough get going – and Keane was nothing if not tough. Indeed, he quite literally rose to the occasion, hauling United back into the contest with a fine near-post header midway through the first half.

Keane then set about taking charge of the midfield in typically abrasive and snarling fashion. His aggression earned him a booking, which ruled him out of the final. Completely undeterred, the combative Corkonian did not burst into tears like a self-obsessed man-child and instead redoubled his efforts to lay the platform for the most significant European win of Ferguson’s tenure.

Keane’s endeavour did not go unrewarded, with in-form strike duo Dwight Yorke and Andy Cole coming up with the goals which saw United blaze their way into their first European Cup final since 1968 in fittingly flamboyant fashion.

2. INTER 1-5 ARSENAL
2003-04


If Keane was at the peak of his powers during the 1998-99 campaign, the same could be said of Thierry Henry in 2003-04. The star attraction in Arsenal’s team of ‘Invincibles’, the Frenchman, with his intoxicating mix of pace, power and panache, was a genuine pleasure to behold in full flight and is arguably the finest overseas player ever to feature in the English top flight.

Indeed, unlike his compatriot Eric Cantona, Henry was a genuine world-class performer, a player who excelled on the grandest stages. Nowhere was this better exemplified than at San Siro on November 25, 2003.

Arsenal arrived at the Giuseppe Meazza for their Group B clash with Inter desperately needing a victory to keep their qualification hopes alive, having been routed by the Nerazzurri at Highbury on matchday 1, before picking up just four points from three games against Lokomotiv Moscow and Dynamo Kiev (home and away).

The Gunners realised their goal – and in scintillating style. Henry opened the scoring with a characteristically precise side-footed finish after a one-two with Ashley Cole and although Christian Vieri drew the hosts level against the run of play with a desperately fortuitous deflected effort shortly before the break, Freddie Ljungberg deservedly put Arsenal back in front just after the restart.

Henry sealed Arsenal’s victory with nine minutes remaining with a perfect illustration of his remarkable athleticism, streaking away on the counterattack only to come to a stop on the edge of the area, stand Javier Zanetti up before cruising past the Argentine with a stunning and seemingly effortless acceleration of pace. The left-footed strike which followed was as powerful as it was precise.

Utterly shell-shocked, Inter conceded two more goals in the closing stages, to Edu and Robert Pires, as Arsenal claimed what should have been their breakout victory in the Champions League. As it was, they bowed out in the quarter-finals to Claudio Ranieri’s Chelsea.

3. AC MILAN 3-3 LIVERPOOL (Liverpool won 3-2 on penalties)
2004-05


If one man embodied whatever it was that propelled a terribly average Liverpool team to Champions League glory in 2005, it was captain Steven Gerrard. The heart and soul of the Reds line-up, the all-action England midfielder had dragged his side into the knockout stages with a stunning late strike against Olympiakos which has already achieved mythical status at Anfield.

Many felt, quite understandably, that Gerrard’s wonderful half-volley against the Greeks would be the highlight of what was then-coach Rafa Benitez’s first season at the helm. However, there was more drama to come from both Gerrard and Liverpool – much more.

After easing past Bayer Leverkusen in the last 16, the Reds then eliminated Juventus in the quarters before reaching the final against all the odds courtesy of a “ghost goal” from Luis Garcia in the second leg of their semi-final clash with Chelsea.

Even then, most pundits felt Liverpool stood little chance of overcoming a fine AC Milan side boasting world-class talent in almost every position and by half time, it seemed that not only would the Premier League side lose in Istanbul, they would also be humiliated.

Indeed, the Anfield outfit had found themselves three goals down after 45 minutes of wondrous football from the Rossoneri. Paolo Maldini opened the scoring with an early volley, Hernan Crespo tapped in a second on 39 minutes, and then producing a fittingly sublime finish to the most sumptuously-weighted through ball from Kaka just before the interval to seemingly put Milan out of sight.

Certainly, the Rossoneri felt the game was done and dusted – at least according to Gerrard, who subsequently claimed that he saw some of the Italian side’s players waving to family and friends as they walked off the pitch at half-time.

Whatever the veracity of that accusation, Gerrard played like a man possessed in the second period and set about turning the game around. Liverpool’s ‘Roy of Rovers’ pulled a goal back with a terrific looping header and then, after Dida had made a mess of trying to keep out Vladimir Smicer’s low drive from distance, Gerrard surged into the Milan area to win a controversial penalty from which Xabi Alonso – eventually – levelled the game. Even more remarkable than the fact that Liverpool had drawn level was that they had done so in a six-minute spell.

Milan regrouped and eventually reclaimed control of the game but Liverpool were not to be denied their fifth European Cup, Jerzy Dudek producing a miraculous save at point-blank range to deny Andriy Shevchenko in extra-time before saving the Ukrainian’s penalty in the shoot-out which followed to clinch a most remarkable victory for the Reds.

4. AC MILAN 3-0 MANCHESTER UNITED
2006-07


Kaka had not deserved to be on the losing side that night in Istanbul, if for no other reason than that beautifully measured ball in behind the Liverpool defence for Crespo. However, by that point the Brazilian was not quite the finished article. Two years later, he was the finest player in the world, as he proved during Milan’s semi-final clashes with Manchester United during his side’s 2006-07 Champions League campaign.

The attacking midfielder, who prefers to glide rather than run, was at his majestic best during the first leg at Old Trafford, scoring two priceless away goals in a 3-2 defeat, the second of which memorably resulted in Gabriel Heinze and Patrice Evra colliding in comical fashion as they tried in vain to halt the former Sao Paulo man’s progress. Not since Ronaldo’s hat-trick for Real Madrid in 2003 had an opposition player produced such a magical performance at ‘The Theatre of Dreams’.

Still, for all Kaka’s brilliance, Milan still had a deficit to overturn in the return leg at San Siro. The pouring rain which greeted the players as they took to the field at the Giuseppe Meazza did not appear to bode well for the Rossoneri’s hopes of turning the tie around but in spite of the conditions, the hosts, inspired by their No. 22, put on an exhibition.

Kaka opened the scoring just 11 minutes in with a left-footed strike from the edge of the box after being brilliantly teed up by Clarence Seedorf, who then doubled Milan’s advantage on the half hour with a well-struck volley.

Alberto Gilardino
put the tie beyond United with a breakaway goal on 78 minutes as Milan secured a deserved shot at redemption against Liverpool in the final, one which they took courtesy of a Filippo Inzaghi double.

5. TOTTENHAM HOTSPUR 3-1 INTER
2010-11


When Gareth Bale travelled to San Siro with Tottenham on October 20, 2010 and announced himself to the world with a second-half hat-trick in a 4-3 defeat by Group A rivals Inter, the hosts could at least claim afterwards that they had not had a full appreciation of the threat posed by the Welshman’s pace and terrific left foot.

They had no such defence after the return clash at White Hart Lane just under a fortnight later. In fact, they had no defence at all. Certainly, Nerazzurri right-back Maicon never showed up – or perhaps more accurately, he wished he hadn’t.

Bale terrorised the Brazilian to such an extent that it actually became difficult to watch. This, after all, was one of the best full-backs in the world being humiliated before a global audience time and time and time again. In truth, what was going on elsewhere on the field of play became something of a sideshow.

Rafael van der Vaart opened the scoring 18 minutes before Peter Crouch deservedly doubled Spurs’ lead on the hour after finally gobbling up the latest delicious delivery from the left-hand side from Bale.

Samuel Eto’o
, the one Inter player to perform on the night, pulled a goal back for the European champions nine minutes from time but the Cameroonian’s strike only resulted in the visitors pressing further forward in the closing stages, thus leaving more space for Bale to exploit.

He did so to stunning effect with just over 60 seconds of normal time remaining, covering some 70 metres down the left flank before whipping the ball over for Roman Pavlyuchenko to tap home and put the result beyond all doubt.

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