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The Incredible History of Man United v AC Milan

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Crespo runs the show in 2005 (Aggregate: Milan 2-0 United)

The stars on show in this round of 16 tie were unbelievable, with both sides starting an insane amount of riches. United had the likes of Cristiano Ronaldo, Roy Keane and Ruud van Nistelrooy among their ranks, while Milan fielded Andrea Pirlo, Kaka and Paulo Maldini, to name just a few.

It was former Chelsea striker Hernan Crespo who made the headlines, as he scored a goal in each leg, handing the Italians a 2-0 win on aggregate, ironically, whilst he was on loan from the Blues. During a cagey encounter at Old Trafford in the first leg, Carlo Ancelotti’s side had more of the ball and more chances, but couldn’t find a way to unlock a resilient United defence.

However, after goalkeeper Roy Carroll spilled an effort from Clarence Seedorf, Crespo was on hand to tap in the rebound, handing the Rossoneri a 1-0 lead to take back to the San Siro. Much like the first leg, Milan were able to limit United’s attacking prospects, despite Sir Alex Ferguson naming van Nistelrooy, Ronaldo, Paul Scholes, Wayne Rooney and Ryan Giggs in the same XI for only the second time. Once again it was Crespo who was the thorn in Fergie’s side, as United were condemned to an early Champions League exit.

United v Milan Prediction

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Alex Telles to assist @ 5/2

Kaka seals the Ballon d'Or (Aggregate: Milan 5-3 United)

Two years later and it was the Italian champions who emerged victorious once again, as AC Milan picked up a 5-2 aggregate win. Many of the same stars from the fixture two years earlier were playing once again, but this time it was Milan’s Brazilian playmaker who would steal the show, following a classic performance at Old Trafford in the first leg. United held the advantage after the first leg, after a 3-2 thriller which saw Wayne Rooney score a winner in added time after going 2-1 down.

The goal of the game came from Milan's midfielder Kaka, who was able to flick the ball over Darren Fletcher, nod past two oncoming defenders and coolly slot past Edwin van der Sar in goal.

The second leg, however, was not as joyful for the Premier League side, as goals from Clarence Seedorf, Kaka and Alberto Gilardino sent United home with a 3-0 loss and a lesson in European football. The game was once again dominated by Kaka, who eventually went on to win the 2007 Ballon d’Or following his Champions League heroics, as Ferguson’s side just couldn’t handle him. Milan would go on to face Liverpool in the final, avenging their defeat from two years earlier and reclaiming Europe’s top prize.

Beckham's return and Rooney's domination (Aggregate United 7-2 Milan)

Finally, after two Champions League defeats to Milan in the previous six years, United toppled the Italian giants and in convincing fashion, coming away with a 7-2 aggregate win. Wayne Rooney was the star for United once again, as he scored a brace at the San Siro in the first leg, before scoring twice more in the reverse fixture. The first game started poorly for United, as Ronaldinho made his mark, creating a number of chances and scoring the first goal, volleying in via a deflection.

However, Scholes was able to convert a Fletcher cross, before Rooney made the game his own with two well-taken goals, in a season of great individual success for the Englishman. At Old Trafford, United made sure of their Champions League progression, hammering Milan by four goals to nil, with a Rooney double accompanying goals from Ji-Sung Park and Fletcher.

The occasion also marked a return to Old Trafford for David Beckham, who had been instrumental in a successful European campaign with United in 1999 and despite a warm reception from the home fans, Beckham flew back to Milan disappointed, as his side crashed out of Europe.

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Bruno Fernandes to score and United to win @ 7/4

Milan beat the holders United in 1969 (Aggregate: Milan 2-1 United_

Manchester United boasted some of the finest footballers in Europe in 1968, as they won their first European Cup under manager Matt Busby. Three of their starting side had won the Ballon d’Or in the 60s, with Denis Law, Bobby Charlton and George Best making up one of the best attacking trios English football has ever seen.

However, they were not so successful the following year, as they met Milan in the semi-finals of that year's competition. Milan edged the first leg 2-0, thanks to goals from Angelo Sormani and Kurt Hamrin, marking a miserable trip to the San Siro for United. Despite a Bobby Charlton goal handing United a 1-0 win at Old Trafford, the damage was done from the first leg and the Red Devils’ defence of the European Cup was over.

AC Milan would go on to face Ajax in the final, cruising past the Dutch side with a 4-1 win and United would not put up another decent challenge for the European title for 30 years.

By Luke Feather