When was the last time AC Milan didn't qualify for the Champions League knockout stage?

European football and the Champions League in particular just wouldn’t be the same without AC Milan. One of the aristocrats of continental football, they were the first Italian club to take part in the former European Champion Clubs Cup, making their debut against FC Saarbrücken in the inaugural tournament way back in November 1955. However it wasn’t the most promising of starts – they ended up losing 3-4 at San Siro with Herbert Martin putting the spoilers on the night for the Italians with a second half winner. Milan did get their own back though, thrashing the Germans 1-4 when they returned for the second leg three weeks later.

In that 1955/5 edition, even after a nervous start, Milan made it all the way to the semi-finals only to be denied a place in the final by the eventual champions, Real Madrid.

Milan crowned Champions of Europe for the first time

Milan lifted the trophy for the first time in 1963 after coming close five years earlier when they were beaten by Real Madrid at Heysel. After Madrid, they are the second most successful club in the history of the European Cup/Champions League with seven titles compared to Madrid’s 13. They are tied with Bayern Munich in final appearances – they have gone all the way 11 times, ending as runners-up in 1958, 1993, 1995 and 2005.

The Rossoneri have generally always made it past the early rounds of the competition – even when it was rebranded and a group stage format was introduced in 1991. There have been just three times when Milan have failed to make it past the group stage and into the knockout stage.

The first time they bowed out early was in the 1996/7 edition – they lost at home to Porto and Rosenburg and finished third on seven points, two points behind the Norwegians and for the first time experienced the miserable feeling of not being in the Last 16 draw.

To the horror of the fans, the same thing happened in the following year when UEFA introduced two group stages (that idea was swiftly abandoned, too many games killed the spirit of the competition). In 1999/2000 Milan were drawn in Group H with Galatasaray, Hertha Berlin and Chelsea. Out of the six group games, Milan won just one – the Matchday 2 meeting with Galatasaray. They ended humiliated in last place, not even qualifying for the UEFA Cup.

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The last time Milan failed to advance to the Last 16

A year later, in 2000/1, Milan, with Alberto Zaccheroni still in charge, did at least manage to make it past the first group stage but more disappointment followed in the second group stage where they drew four out of their six games – including all three of their home games. They finished third behind Deportivo and Galatasaray and once again, missed out on the last 16.

The Italians were regulars in the latter stages of the Champions League for the next seven editions and lifted Ol’ Big Ears in 2003 and 2007. Milan have taken part in 18 editions of the Champions League and only failed to advance past the group stage on three occasions.

This year, there is a chance they could miss out again. They have to win their final match whatever happens in the other game. The team is third in Group B on four points, level with Atlético Madrid (with a marginally better goal difference) and one point behind Porto who are second. On the plus side, they face Liverpool who are already through to the next round as champions of the group – and also they will be playing at home.

To secure second place they must beat Liverpool and hope Porto either draw or lose at home to Atleti. If Atlético win at the Dragão, and Milan beat Liverpool, they will be tied on seven points and the runners-up place would be decided on goal difference and if they are still level after that, the team to have scored the most goals in the group stage would advance.