Manchester United vs AC Milan Tickets

These two European behemoths have a collective ten European Cup/UEFA Champions League titles and can rightly be considered among the biggest teams on the continent, and that makes this battle one well worth seeing in the flesh.

The two clubs have a long shared history in the competition. They first met in May 1958 in the Semi-Final of the European Cup, and goals from Dennis Viollet and Ernie Taylor gave United a 2-1 home win to take to the San Siro, which was not enough.

AC Milan made light work of their visitors and won 4-0 to set up a final with the all-conquering Real Madrid side of the era, where they lost 3-2 after extra time in Brussels.

The Italian side did win their first European Cup soon after, defeating Benfica in 1963, and in 1968, Manchester United also beat the Portuguese giants to win their first title at Wembley Stadium.

In 1968-69, AC Milan and Manchester United were once again lined up against each other in the Semi-Finals. This time, the San Siro side started with a 2-0 home win from the first leg before Bobby Charlton pulled one goal back at Old Trafford with 20 minutes to play, but Sir Matt Busby’s side could not complete the job, and Milan then thumped Ajax in the final, 4-1 in Madrid.

AC Milan then waited another twenty years before winning the competition again, this time thrashing Steaua Bucharest in the final, with Dutch pair Ruud Gullit and Marco van Basten both scoring twice in a 4-0 win in Barcelona.

The following year, they edged Benfica 1-0 in Vienna when the third of their famous Netherlands trio, Frank Rijkaard, scored the only goal of the game to give boss Arrigo Sacchi another title.

During this period, Manchester United had missed out on competing at this level, with Sir Alex Ferguson still looking to take his side back to the domestic title, something they finally managed in 1992/93.

Meanwhile, AC Milan suffered a surprise loss to Marseille in the 1992 UEFA Champions League but bounced back to annihilate FC Barcelona 4-0 in the 1994 final under Fabio Capello.

The following season, they lost to an impressive young Ajax side in the final, and in 1999, Manchester United ended their thirty-year top-tier European crown drought when they famously came from behind to beat Bayern Munich in injury time.

2002/03 saw AC Milan defeat Juventus on penalties to win the club’s sixth title, and the two teams went head to head again in 2004/05, a UEFA Champions League campaign that the Rossoneri may want to erase from their collective memory.

The two faced each other in the Round of 16, and a Hernan Crespo goal gave them a vital away win in the first leg, and the Argentine did likewise in the return. They then beat city rivals Inter Milan in the Quarter-Finals and then PSV Eindhoven in the Semi-Finals to then meet Liverpool in Istanbul.

Carlo Ancelotti’s side then eased to a 3-0 lead at half-time, and the game looked dead and buried before captain Steven Gerrard pushed his side to a miraculous recovery with the game tied at 3-3 after extra time, forcing the game into a penalty shoot-out.

Serginho, Andrea Pirlo, and Andrei Shevchenko all failed to net, and Rafa Benitez’s men, therefore, completed one of the most astounding UEFA Champions League victories of all time.

Two years later, AC Milan gained revenge for that loss by beating Liverpool in the 2006/07 UEFA Champions League Final 2-1. On the way to doing so, they beat Manchester United 5-3 on aggregate in the Semi-Finals.

The following season, Manchester United defeated Chelsea on penalties to get their third title.

Manchester United vs. AC Milan Head-to-Head

In 2009/10, Manchester United faced AC Milan once again, this time in the Round of 16. In the first leg in Italy, Wayne Rooney scored twice to give the Premier League side a 3-2 lead to take back home.

In the second leg, Rooney scored twice again, and Ferguson’s side eased to a 4-0 victory, but they were then knocked out by Bayern Munich in the next round.

Ferguson’s side lost the UEFA Champions League Finals to Barcelona in the 2009 and 2011 finals, and since the Scot left the managerial post, Manchester United have struggled in the competition.

Indeed, since 2011, neither team has made it as far as the final of the competition, though, in 2023, AC Milan did get to the Semi-Finals, only to lose to local rivals Inter 3-0 over the two legs.

In 2020/21, the two sides met in the UEFA Europa League Round of 16, the game ending in a 1-1 draw in England before Paul Pogba scored the only goal of the game in Milan to give Ole Gunnar Solskjaer’s side a path through to the next round. They went all the way to the final that year before losing on penalties to Villarreal in Gdansk, a game that saw 21 successive penalties scored before keeper David De Gea stepped up and saw his effort saved by his opposing number, Geronimo Rulli.

Manchester United vs. AC Milan Connections

A large number of individuals have played for both these giants, and these include Scottish forward Joe Jordan, Diogo Dalot, Zlatan Ibrahimovic, Matteo Darmian, Ray Wilkins, Jaap Staam, Jesper Blomqvist and Massimo Taibi.

Another star to have worn both shirts is David Beckham. The former England captain enjoyed ten years in the first-team set-up at Manchester United, playing a total of 394 games for the club and scoring 85 goals.

The midfielder won six Premier League titles and a host of other items of silverware and played a key part in the club’s 1999 UEFA Champions League success, providing the corners that led to both goals.

He left United for Real Madrid in 2003 and then played in the United States before spending two spells out on loan at AC Milan. He made 33 appearances in those two stints, scoring two goals across 2008/09 and 2009/10; he bowed out of the game at Paris Saint-Germain in 2013.