Andrea Pirlo battles with Darren Fletcher when Man Utd last played Milan at Old Trafford in 2010

United set to renew old rivalry with Milan

Friday 26 February 2021 12:30

Manchester United will renew an old rivalry when we meet AC Milan in the Europa League's Round of 16.

Ahead of the clashes on 11 and 18 March, we’re reflecting on some of our classic encounters with the Serie A giants, including the 10 competitive meetings so far which have resulted in five wins apiece.


We first locked horns with Milan in the 1957/58 European Cup semi-finals, just three months after the tragedy of the Munich Air Disaster. In the first leg at Old Trafford, it was the Italians who took the lead, via Juan Schiaffino. However, under assistant manager Jimmy Murphy’s diligent guidance, the Reds eventually came back to win 2-1 on the night, thanks to goals from Dennis Viollet and Ernie Taylor. It was a different story in the return leg six days later, when United lost 4-0 in a hostile San Siro atmosphere, as the hosts moved onto the final.
United goalkeeper Harry Gregg punches away a Milan cross at Old Trafford in 1958.
A similar fate befell United 11 years later, when again the Rossoneri eliminated us at the last-four stage. On this occasion, United - as European champions - were beaten 2-0 in the first leg, before Milan travelled to Old Trafford for the decisive return fixture. Despite Sir Matt Busby’s Reds dominating the game, we could only nick one goal, through Bobby Charlton. The Serie A side therefore progressed to the 1968/69 final, one they would ultimately win 4-1 against Ajax.

After missing each other in European competitions for 36 years, United and AC Milan were drawn together in the Champions League's last 16 in 2004/05. The first leg in Manchester was a tense affair, one which had been billed as Jaap Stam’s return to Old Trafford, only for the Dutchman to pick up an injury in the warm-up. Without him, Carlo Ancelotti’s men still won 1-0, thanks to Hernan Crespo’s predatory finish. The Argentinian, on loan from Chelsea at the time, again proved to be the difference in the return leg, with the striker grabbing the only goal of the game and securing Milan’s place in the last four. 

We were paired with the Italians again in Europe’s elite tournament just two years later. It was the third semi-final to be contested by the clubs and United were aiming to undo our wretched record against the Rossoneri. With superstars in both line-ups, Cristiano Ronaldo put Sir Alex Ferguson's side ahead in the first leg, only for a Kaka brace to send us in at the break trailing. A Wayne Rooney double turned that around, with his second strike coming in injury time to seal a fantastic 3-2 victory. But again it wasn’t meant to be, as Milan triumphed 3-0 a few weeks later to progress to the 2006/07 final, where they would beat Liverpool 2-1 in Athens.
Rooney celebrates his late winner in 2007 - but Milan had the last laugh in the second leg.

Our most recent double header with Milan came at the start of the last decade, when the Reds finally overcame our hoodoo against the Serie A outfit. A 3-2 win at the San Siro in the first leg of the Champions League last-16 clash in 2009/10 set us up perfectly for the reverse fixture at Old Trafford - and it was one to remember for our supporters.

With David Beckham back at the Theatre of the Dreams for the first time, United put on a superb showing and blew Milan away, running out 4-0 winners courtesy of goals from Rooney (2), Ji-sung Park and Darren Fletcher. Sadly our campaign ended in the next round, as Bayern Munich beat us on aggregate in the quarter-finals.

Beckham received a warm reception from the United fans - and former team-mate Gary Neville - in 2010.

Milan have also been familiar opponents on the friendly circuit, particularly in recent years. Further back, United welcomed Ruud Gullit, Marco van Basten and co to Old Trafford for an end-of-season friendly in 1988, when the visitors lived up to their reputation as a European powerhouse. The Rossoneri were three up within 67 minutes thanks to goals from Pietro Paolo Virdis and Claudio Borghi (2), which rendered Jesper Olsen and Brian McClair’s strikes irrelevant.

Ahead of the 2004/05 campaign, the Reds met Milan in New Jersey, with Paul Scholes and Andriy Shevchenko netting in a 1-1 draw. The game then went to a penalty shootout, which Milan won after a remarkable 20 spot-kicks. In an unusual twist, United goalkeeper Tim Howard was the man responsible for the decisive miss.
Our most recent game against Milan actually came in the summer of 2019, when we met them as part of our pre-season tour. In our last warm-up game ahead of the new season, Jesse Lingard and Marcus Rashford were on target during a 2-2 draw that forced another penalty shootout. On this occasion, it was United who emerged victorious after we converted all five spot-kicks.