From Istanbul to Athens: How AC Milan and Liverpool Made Champions League History

When it comes to European prestige, AC Milan and Liverpool are unquestionably two of the continent’s most revered clubs, with 13 European Cups/Champions League titles between them.

In 1963, Cesare Maldini captained the Italians to their first, his son Paolo to their most recent 44 years later. Bob Paisley, meanwhile, is considered a Reds immortal for clinching the European Cup three times between 1976 and 1981.

But it was only after the turn of the century that these two powerhouses finally met on the biggest stage in 2005. Nineteen years have passed since that incredible night in Istanbul when Jerzy Dudek – the master of distraction – dragged Liverpool to penalty shootout glory, a bizarre tale as preposterous as Adam Sandler’s Waterboy script.

Carlo Ancelotti and Paolo Maldini would get their revenge in 2007. This time, there was no first-half obliteration or second-half miracles, just a run-of-the-mill cliche Italian performance with two goals from the craftiest striker of his generation.

Peeling away from Liverpool’s wall, Filippo Inzaghi intentionally deflected Andrea Pirlo’s free-kick past Pep Reina, then beat Jamie Carragher’s offside trap to slide his effort under the Spaniard for his second. There were jitters, but Don Carlo’s side held on in Athens despite the late scare – a Dirk Kuyt header – and lifted Europe’s greatest prize for the seventh time.

Revenge was sweet for Maldini and Milan fans, and it was enough to exorcise the demons for a while. Yet, years on, the sickening feeling of 2005 still lingers deep in the stomach, and the prefrontal cortex struggles to process what unfolded that night in Istanbul.

When asked about Liverpool, most Milanisti recall the shocking shootout defeat. Understandably, many quit following football altogether after that fateful night, like our esteemed friend, Andrea, who spat the dummy and turned to water polo.

Indeed, the mere thought of a Champions League match against Liverpool is enough to induce a bout of post-traumatic stress disorder, and, in 2021, Milan twice again came undone in the group stage, losing by a goal at Anfield and later at the San Siro during Stefano Pioli’s tenure.

On matchday six, the two heavyweights met at the Stadio Giuseppe Meazza for the first time. Fikayo Tomori opened the scoring, quickly knocking in a loose ball. Mo Salah obliged by doing the same in the second half, and Divock Origi’s header took Liverpool into the lead when Tomori gave possession away under pressure.

Denying Frank Kessie with five minutes to go, Alisson Becker celebrated his 150th appearance by winning it for the Reds. They became the first English club to win all six group-stage matches. Three years later, the Brazilian returns to Italy knowing the tables could be turned.

“Before us, there is a historic club,” Alisson told RAI Sport. “We know that these two teams, Liverpool and AC Milan, always compete in great finals and matches. There have been a couple of them in the 2000s.”

This will be the fifth time Milan and Liverpool meet, but only the second time they’ll face each other at the San Siro. Adding to the drama, new signing Federico Chiesa is in line to make his Liverpool debut. The Italian, who scored 21 Serie A goals at Juventus, has lacked match fitness and missed the 1-0 loss to Nottingham Forest on the weekend.

Chiesa, who missed Italy’s Nations League victories, could come off the bench at the Meazza, the venue where he produced a match-winning display for Juventus in 2021, scoring a goal in each half. For Fiorentina, Chiesa either scored or assisted in all four matches away against Milan, registering three assists and two goals.

Liverpool manager Arne Slot celebrates his birthday today, and the Dutchman hinted that Chiesa could feature.

“So I don’t think you should expect him to start but he will make some minutes if we needed him,” Slot told us. “I don’t expect him to start with us. He’s had some training time and too early to play 90 mins but hopefully some minutes in the upcoming fixture.”

Pressure is building for Milan boss Paolo Fonseca, who finally won his first Serie A match in charge of the Rossoneri against bottom-side Venezia. The problems are mainly in defence for the Portugese, who conceded six times in the opening three weeks. Up front, compatriot Rafa Leao (one goal, two assists) must show his quality alongside Christian Pulisic (two goals, two assists) if Milan are to stand a chance.

Former midfielder – and victim of the 2005 Final – Clarence Seedorf weighed in. “Leao is the master of his destiny, Seedorf told La Gazzetta dello Sport. “He has talent, so he must use it to become one of the best.”

Fonseca could use someone of Seedorf’s calibre. How times have changed since the pedigree of the Silvio Berlusconi era: Milan have only qualified for a semi-final once in that time, in 2023, when they were thumped by Inter. And the Nerazzurri are waiting for them in the Derby della Madonnina this Sunday (we’ll be there for that).

Clearly, the Ancelotti dynasty yielded more pleasure than pain, at least in terms of finals. Having won the European Cup twice as a player for Milan, as a manager he led the Rossoneri to victory over Juventus on penalties at Old Trafford in 2003, then got his revenge against Liverpool four years later.

Our advice? Milan fans should forget revenge – it only eats away at you. Take a leap of faith instead. Let’s cue some epic Champions League classical music and breathe in the match-winning line-up of 2007.

MILAN: 1 Dida, 44 Oddo, 18 Jankulovski, 13 Nesta, 3 Maldini ©, 8 Gattuso, 21 Pirlo, 23 Ambrosini, 10 Seedorf, 22 Kaka, 9 Inzaghi. Coach: Ancelotti. Subs: 19 Favalli, 4 Kaladze, 11 Gilardino. Unused subs: 32 Brocchi, 2 Cafu, 16 Kalac, 27 Serginho.

LIVERPOOL: 25 Reina, 3 Finnan, 6 Riise, 5 Agger, 23 Carragher, 16 Pennant, 14 Alonso, 20 Mascherano, 32 Zenden, 8 Gerrard ©, 18 Kuyt. Coach: Benitez. Subs: 15 Crouch, 2 Arbeloa, 7 Kewell. Unused subs: 4 Hyypia, 1 Dudek, 11 Gonzalez, 17 Bellamy. 

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