Classic matches between Manchester United and AC Milan

It's been 11 years since Manchester United last drew AC Milan in a European competition, and the two famous old clubs will come face to face once more in the round of 16 of this season's Europa League.

The sides have played each other ten times throughout their illustrious histories and each have come out on top on five occasions. The 11th and 12th meetings will occur next month, with a spot in the Europa League quarter finals the prize.

It's the first time United and AC Milan will battle it out in a competitive setting outside of Europe's elite club competition but, with both hitting hard in their respective domestic league once more, it still promises to be a thrilling affair.

So, in preparation, let's go down memory lane and remember some of the best meetings between the two.

Manchester United 2-1 AC Milan - 8 May 1958

The Munich air disaster occurred on 6 February 1958, shocking the entire world and seemingly ripping the soul out of Manchester United who suffered 12 fatalities - eight of whom were players.

United would go on to win just once in the league after the event, finishing ninth in the first division. Remarkably, however, just over three months after the crash, the Red Devils overcame AC Milan in the first leg of the European Cup semi finals with a 2-1 win. Dennis Viollet, who survived the crash, got the equalising goal to set up the comeback on the day.

Unfortunately, the second leg resulted in a 4-0 defeat to a Milan side who would go on to lose 3-2 to Real Madrid in the final.

Manchester United 3-2 AC Milan - 24 April 2007

A classic Champions League match.

Despite United coming out on top on the night, it was a vintage performance from Kaka that stole the show. The Brazilian magician overturned an early Cristiano Ronaldo strike with two goals of his own in the first half, including one of his most iconic moments - skip to 2:05 in the above video to see just how untouchable he was in his prime.

It was, however, a second half Wayne Rooney brace that gave United the win. The Red Devils legend scored in the 59th minute before stealing it in the second minute of stoppage time to take a 3-2 lead to Milan.

AC Milan 3-0 Manchester United - 2 May 2007

The second leg didn't go as planned for Sir Alex Ferguson.

Kaka (again), Clarence Seedorf and Alberto Gilardino goals sealed a resounding 3-0 win to book a place in the 2007 Champions League final, where the Rossoneri would meet Liverpool.

Milan beat the Reds 2-1 in the final to get their seventh title and exact their revenge for what happened in Istanbul two years earlier.

AC Milan 2-3 Manchester United - 16 February 2010

Manchester United achieved their first ever away win against Milan in the first leg of their Champions League round of 16 tie in 2010.

History looked to have be repeating itself when Ronaldinho put Milan in front after connecting with David Beckham cross (weird, I know). But a Paul Scholes strike and a Rooney double before Seedorf's beautiful consolation goal gave Ferguson's men a lead going into the second leg.

Ah, we've been here before, haven't we?

Manchester United 4-0 AC Milan - 10 March 2010

But United finally saw the tie through!

Beckham's return to Old Trafford wasn't exactly fruitful, as his side left having been thumped 4-0, giving the tie a whopping 7-2 aggregate score line.

Yet another Rooney brace and goals from Park Ji-sung and Darren Fletcher sent United comfortably into the quarter finals, where they would eventually be knocked out on away goals by Bayern Munich.

AC Milan 1-1 Manchester United (8-9 on penalties) - 25 July 2018

Okay, it was a pre-season friendly. And, okay, it ended 1-1 with a penalty shootout deciding the outcome.

But 9-8! With 26 penalties taken! That's just pure entertainment.

Now, you should never miss a penalty. But if you do, do it like Franck Kessie did to lose his side the game just after Ander Herrera had scored his second of the night to make it 9-8.

Oh, Franck.