Manchester United and AC Milan have won nine European Cup and Champions League titles between them, while they have played in 16 finals overall.
Their meeting over two legs in the Europa League last 16 next month will be the tie of the round, with both former heavyweights finally now heading in the right direction to get back to their respective former glory.
In 2007, these two played each other over two legs in a Champions League semi-final and were arguably the two best sides in Europe at the time. Truth be told it would have been a more fitting final than the one we got in reality, which was Milan versus a Liverpool side that finished 19 points adrift of United in the Premier League that season.
On that occasion, a Wayne Rooney-inspired United won 3-2 in a modern classic at Old Trafford. But eventual 2007 Ballon d’Or winner Kaka, who had scored twice in Manchester as it was, pulled the strings on a wet night in the return leg in Milan as the Rossoneri won 3-0 to go through.
In 2005, a truly majestic Milan team had knocked United out of the Champions League at the last 16 stage, winning 1-0 home and away thanks to second half goals from Hernan Crespo.
In 2010, another last 16 meeting in the Champions League saw United take revenge. Rooney again enjoyed one of the nights of his life, scoring twice at San Siro in a 3-2 away win. That game is also particularly remembered for Park Ji-sung pocketing Andrea Pirlo, completely stifling Milan’s deep-lying play-maker and never giving him a single moment of peace.
In the return leg, Milan crumbled and United cruised to an emphatic 4-0 win.
The history between United and Milan at European football’s highest level goes almost all the way back to the very beginning of the European Cup. Already at that time, they were continental giants, with Milan reaching the semi-finals in the inaugural European Cup season in 1955/56 and United also getting to the last four at their first attempt in 1956/57. Both were knocked out by Real Madrid.
The first time these clubs met in the European Cup was a poignant semi-final tie in 1958. It came three months after the Munich air disaster that had tragically killed eight United players, having successfully secured a place in the last four after knocking out Red Star Belgrade.
The first tie was originally scheduled for April but was delayed by a month because of the impact of the crash. Remarkably, a patched up United side won 2-1 at Old Trafford, although Milan prevailed 4-0 in the return, with 1950 World Cup winner Juan Alberto Schiaffino scoring twice.
United and Milan met again in the European Cup semi-finals 11 years later, by which time both clubs had already lifted the iconic trophy. Milan won it in 1963 following years of early Real Madrid and then Benfica dominance, becoming the first Italian club to do it. United soon followed suit in 1968 when they were crowned England’s first ever European champions.
The Red Devils were actually the reigning champions when they faced Milan in 1969, although it was the Rossoneri that won 2-1 on aggregate and went on to lift the trophy a second time when they subsequently beat an emerging Ajax side in the final.
2020/21 represents the first time that Manchester United and AC Milan will have played each other in Europe’s secondary competition and it is an indicator of how far each club has fallen in the last decade, with both former giants only seeing seeds of genuine recovery relatively recently.
Neither has won a domestic league title since 2013, with Milan’s most recent success in 2011. Yet both clubs are improving and currently sit second in their respective countries. A serious title challenge for United this season seems one step too far, but the promise is there, while Milan were setting the pace in Serie A until a recent blip allowed city rivals Inter to get ahead.
This season’s Europa League last 16 will not be a case of two heavyweights going toe-to-toe at their peak, but it will be a window back into the past of what once was and also a tantalising glimpse into the future of what might again be.