AC Milan are only joint second (with neighbours Inter) in the list of Italian champions behind Juventus. But Associazione Calcio Milan (to give them their full title) have won more European Cups/Champions Leagues than any other Italian side, and by some distance. In fact, only Real Madrid have been crowned European champions more times than Milan and the Italian side’s seven triumphs put them one ahead of both Liverpool and Bayern Munich, two ahead of Barcelona and four ahead of their nearest Italian rival, their housemates at the San Siro, Inter Milan.
In this article, we’ll give information about Milan’s seven European Cup/Champions League successes and we’ll also outline what happened on the four occasions they ended as runners-up in the tournament. Finally, we’ll run through some of Milan’s biggest upsets and worst performances when playing at the top table of European football.
When Did AC Milan Last Win the Champions League?
AC Milan last conquered the Champions League in 2007 when they beat Liverpool 2-1 in the final at the Olympic Stadium in Athens. It was revenge of sorts for the final of 2005 (dubbed the Miracle of Istanbul) when Liverpool came back from 3-0 down against Milan to draw level and eventually win on penalties. Carlo Ancelotti’s men didn’t need penalties in 2007 though, a brace from Filippo Inzaghi proving enough to topple the Reds.
Champions League Finals
As well as their seven victories, Milan have also finished as runners-up four times, which gives them a decent win rate in the final of almost 64%. Although that is significantly lower than that of Real Madrid who have won 82% of their 17 finals! Based on the below table, it’s clear Milan had something of a purple patch from 1989 to 1995, a period in which they won the tournament three times and ended as runners-up twice.
| Year | Opponent | Result | Score |
|---|---|---|---|
| 2007 | Liverpool | Won | 2-1 |
| 2005 | Liverpool | Lost | 3-2 on penalties (3-3 after 90 minutes and extra time) |
| 2003 | Juventus | Won | 3-2 on penalties (0-0 AET) |
| 1995 | Ajax | Lost | 1-0 |
| 1994 | Barcelona | Won | 4-0 |
| 1993 | Marseille | Lost | 1-0 |
| 1990 | Benfica | Won | 1-0 |
| 1989 | Steaua București | Won | 4-0 |
| 1969 | Ajax | Won | 4-1 |
| 1963 | Benfica | Won | 2-1 |
| 1958 | Real Madrid | Lost | 3-2 (AET) |
Stage of Elimination
Milan have appeared in 29 European Cup/Champions League tournaments to date and have made it to the semis or beyond 45% of the time, which is pretty good going by anyone’s measure. Like most sides, they’ve also had one or two early-tournament hiccups over the years but they tend to apply themselves well in the Group Stage and generally manage to make it through to the knockout stages.
| Stage | Number of Times | Percentage |
|---|---|---|
| Won | 7 | 24% |
| Final | 4 | 14% |
| Semi Final | 2 | 7% |
| Quarter Final | 4 | 14% |
| Round of 16 | 7 | 24% |
| Group Stage | 4 | 14% |
| First Round | 1 | 3% |
Note that some rounds and the tournament format have changed over the decades.
Times AC Milan Won the Champions League
AC Milan 2002/03 Champions League Win (Soccer illustrated / Wikipedia.org)
As only Real Madrid have won more European Cups/ UEFA Champions Leagues (UCL) than Milan, there are clearly quite a few to document here. As such, we’ll be relatively brief as we summarise each of Milan’s seven victories.
2007: No Mistake This Time
In a re-run of the 2005 final, Milan faced Liverpool in 2007, but this time the Italians weren’t going to throw away a lead. The Old Lady were managed by Carlo Ancelotti and Liverpool by Rafael Benitez (both of whom would go on to manage Everton), so no change for either side from 2005. But Milan had had a mini clear out on the playing side since their defeat in Istanbul and despite having a little less flare, they were a more solid outfit when the duo met in the Olympic Stadium in Athens.
Milan had already proved their mettle on their way to the final as they’d beaten Bayern Munich and Manchester United (among others). Liverpool, for their part, had got the better of Chelsea and Barcelona on the way to Athens. But on the night it was the Italian side who edged it. They didn’t dominate by any means and actually had fewer shots (five to Liverpool’s 12) and fewer on target (three to four), but two goals from the brilliantly clinical fox in the box Inzaghi in the 45th and 82nd minutes was enough, despite a late Dirk Kuyt consolation.
2003: Hard Fought Victory Against Fellow Italians
Ancelotti was starting to make his mark as Milan boss by the 2002/03 season and though he hadn’t won any silverware, his side was looking impressive. When they made it to the Champions League final at Old Trafford against fellow Italians Juventus, it was Ancelotti’s chance to get one over on his previous side, Juventus.
Although this wasn’t exactly a final for the neutrals, there were some passages of excellent play by both sides and especially from a defensive point of view. There was plenty of attacking talent on display as well though, with the likes of Inzaghi, Andriy Shevchenko and Rui Costa for Milan and Alessandro Del Piero, David Trezeguet and Edgar Davids for Juve, but none could find a goal in normal time or indeed extra time. Milan subsequently triumphed 3-2 on penalties after three Juve players and two from Milan missed their spot kicks.
1994: Milan Masterclass Outdoes Blustering Barca
Sandwiched between two defeats in Champions League finals (to Marseille in 1993 and Ajax in 1995) the 1994 triumph over Barcelona in Athens was a big highlight of Fabio Capello’s reign as Milan boss. Milan faced Johan Cruyff’s Barcelona side that was packed full of world-beating stars including two of the top scorers from the 1994 World Cup (that would occur soon after this final), Romário and Hristo Stoichkov. They also had Pep Guardiola and Ronald Koeman attempting to keep things tight for Barca, but that plan failed miserably as Milan tore their opponents apart in what is considered one of the best ever performances by a club side.
Milan took the lead after 22 minutes through Daniele Massaro, and the man from Monza added another on the stroke of half time. Barca came out after the break looking up for the fightback, but that intent was swiftly quashed when Montenegrin striker Dejan Savićević scored just two minutes into the second half. Marcel Desailly put the icing on the cake for the Italians as he scored the fourth goal, making the Frenchman the first player to win back-to-back European Cups/Champions Leagues with two different clubs (he played for Marseille the year before when they’d beaten Milan).
1990: Rijkaard Hits Right Notes in Vienna
This narrow victory in the European Cup final in Vienna against Benfica showed how dominant this crop of Milan stars had become (after their success in the tournament in the previous season). Italian boss Arrigo Sacchi was in the dugout and he led a team of true winners, not least the top-class Dutch trio of Frank Rijkaard, Marco van Basten and Ruud Gullit. But they had a very good supporting cast too with Carlo Ancelotti, and the brilliant centre back pairing of Franco Baresi and Paolo Maldini, among others, all proving their worth during the course of the tournament.
To be fair to Benfica, they didn’t exactly crumble in the final and they took the game to the Italians. Ultimately, though it was Rijkaard’s 68th-minute goal that proved decisive. The 1-0 victory gave Milan back-to-back triumphs that emulated their city rival Inter’s achievement in the same competition when they won it in 1964 and 1965.
1989: Dutch Masters Turn Screw on Steaua
People looking back at this final might well think it was always going to go the way of Milan given that they were playing against Romanian side Steaua București. But it ought to be remembered that the Romanians had won the European Cup just three years earlier (when they got the better of Barcelona in the final) so they weren’t exactly pushovers.
Having said that, when Milan’s Dutch trio were on song, they were almost unplayable, and so it proved on that evening in Barcelona as Marco van Basten and Ruud Gullit scored two goals apiece to earn Milan their third European Cup and their first since 1969. It was certainly one of the greatest teams in Milan’s history and arguably one of the best in the history of European football, something indicated by the 6-1 (on aggregate) hammering of Real Madrid in their semi final.
1969: Prati Inspires Milan to Pretty Victory Over Ajax
En route to the 1969 European Cup final, Milan beat the 1967 champions, Celtic, and the reigning champions, Manchester United, so there’s no doubt they deserved their place in the showpiece game in Madrid. Their opponents were Dutch side Ajax who featured, among others, a young Johan Cruyff. But the future world beater was well and truly overshadowed on the night by Milan’s Pierino Prati.
Prati, who began his career at Salernitana, scored an impressive hat-trick at the Bernabeu. Prati scored twice in the first half before Serbian centre back Velibor Vasovic got one back from the spot for Ajax. Angelo Sormani scored soon after for Milan to make it 3-1 before Prati completed his hat-trick (and the 4-1 victory) after 75 minutes.
1963: First Italian European Champions
Benfica were a real force in the early 1960s, not least because they enjoyed the services of one of the best players of his era, Eusébio da Silva Ferreira. The Portuguese side had won the European Cup in the two previous seasons and many expected them to make it three in a row when they faced Milan at Wembley Stadium. But Nereo Rocco’s men had other ideas.
It was Benfica who struck first, though, with that man Eusébio scoring after 19 minutes. But the Italians didn’t panic and eased their way back into the game in the second half when Brazilian-turned-Italian, José Altafini, got one back in the 58th minute. There was all to play for and both sides had their chances, but it was Altafini who got the winner in the 69th minute to earn Milan their first European title, making them the first Italian side to go all the way in the European Cup.
AC Milan’s Worst Upsets
canno73 / Bigstockphoto.com
Despite their usually very adept performances in the European Cup and Champions League over the decades, there’s no doubt that Milan have fallen far short of their own high standards on several occasions. One such occasion came in the 1996/97 tournament.
Milan had won the tournament in 1994 and were the losing finalists the following year and still had a very fine side. Their fans were therefore expecting a decent run in the 1996/97 Champions League, but it wasn’t to be. Drawn in a relatively straightforward group alongside Portugal’s Porto, Rosenborg of Norway and IFK Göteborg of Sweden, Milan couldn’t get themselves going and ended up losing a game to each of their opponents. The two victories they mustered were not enough to see them through to the knockout stage of the tournament and thus they were stopped in their tracks.
Things were arguably even worse in the 1999/2000 tournament when Milan finished bottom of their group. They were up against Chelsea, Hertha Berlin and Galatasaray, which perhaps isn’t the easiest draw they could have been handed but was certainly far from the hardest. But they managed just a single victory (at home against the Turkish side) and so didn’t even have the dignity of parachuting into the UEFA Cup as Galatasaray got that “honour”.
One of the biggest “upsets” could arguably be Milan’s 2005 defeat to Liverpool in the Champions League final in Istanbul… at least if you looked at the game at half time when Ancelotti’s men were 3-0 up and looking nailed on to be crowned champions. Miracles do happen, apparently – at least if you’re a Liverpool fan. And, somehow Liverpool battled their way back into the game to take it to penalties, which they won 3-2 to leave Milan wondering what had happened.