AC Milan and Liverpool are second and third behind Real Madrid on the UEFA Champions League’s all-time roll of honour.
The Rossoneri are seven-time champions, while the Anfield club have six. There are seven more European trophies apiece in their cabinets.
Despite their own storied respective pasts, it is a curiosity that the two clubs have only met sparingly on the competitive stage. Tuesday's opening Champions League league-stage match at San Siro will be their fifth overall.
That doesn't mean there is not a rich shared history, however, including perhaps the greatest European final of them all.
WATCH: UEFA Champions League with a FREE trial of Paramount+ in USA | A new era of UEFA Champions League in Australia, only on Stan Sport
Liverpool vs AC Milan head to head
Across the four meetings, Liverpool have two victories to AC Milan's one.
That Italian success came as revenge following a 2005 draw, a game that arguably stands as the Reds' most memorable triumph in their history.
MORE: Teams with the most UEFA Champions League titles
Liverpool vs AC Milan history, past meetings
Liverpool have only faced AC Milan once before at San Siro. Prior to their September 2024 game, half of Liverpool and Milan's competitive meetings had come in Champions League finals.
| Date | Competition stage | Result |
| 05/25/2005 | UEFA Champions League final | Liverpool 3-3 AC Milan (AET; Liverpool won 3-2 on penalties) |
| 05/23/2007 | UEFA Champions League final | Liverpool 1-2 AC Milan |
| 09/15/2021 | UEFA Champions League group stage | Liverpool 3-2 AC Milan |
| 12/07/2021 | UEFA Champions League group stage | AC Milan 1-2 Liverpool |
Liverpool 3-3 AC Milan (3-2 on penalties) — 2005 Champions League final
The Miracle of Istanbul. A match etched into European football folklore really should have been Liverpool's ultimate embarrassment. Before halftime at the Ataturk Olympic Stadium, Rafael Benitez's men were utterly dreadful.
Paolo Maldini volleyed in an Andrea Pirlo free-kick inside the first minute and Milan's imperious midfield diamond of Pirlo, Gennaro Gattuso, Clarence Seedorf and Kaka proceeded to dominate the first half. Liverpool avoided further damage until the 39th minute when Hernan Crespo scored the first of a quickfire brace, the latter created exquisitely by Kaka.
Liverpool headed to the dressing room in disarray and Benitez infamously reconfigured his lineup so that it had 12 players in it. Once that kink was ironed out, on came Dietmar Hamann to give the Reds a foothold in midfield and unleash Steven Gerrard.
The talismanic captain reduced the arrears with a superb 54th-minute header. Within seven minutes, Liverpool were level, Vladimir Smicer scoring a low drive and Xabi Alonso converting the rebound after Dida saved his penalty.
Despite the best efforts of both sides — which included a truly remarkable close-range miss from Milan striker Andriy Shevchenko in extra time — the game when to spot-kicks, where Liverpool goalkeeper Jerzy Dudek was the hero, saving from Pirlo and Shevchenko after Serginho fired over from Milan's first attempt.
Liverpool 1-2 AC Milan — 2007 Champions League final
Two years later, Carlo Ancelotti's side had the chance to settle the score and they did not let it pass them by. Filippo Inzaghi, who missed out to Crespo in Istanbul, was selected to start and the generation's master of scruffy goalscoring inadvertently diverted a Pirlo free-kick beyond Liverpool keeper Pepe Reina on the stroke of halftime.
Eight minutes from time, Kaka picked out Inzaghi to seal glory. Dirk Kuyt pulled one back for Liverpool in the 89th minute to set up a nerve-shredding finish, but there would be no great escape this time.
MORE: All the latest Champions League news | How does the 2024/25 Champions League work? | Full UCL match schedule
Liverpool 3-2 AC Milan — 2021 Champions League group stage
Two goals in quick succession shortly before halftime from Ante Rebic and Brahim Diaz left Liverpool needing another comeback against Milan. A Fikayo Tomori own goal had put Jurgen Klopp's side ahead early on and it could have turned into a very long night for the Rossoneri had Mohamed Salah not had a 14th-minute penalty saved.
The Egyptian superstar made amends three minutes after halftime before Jordan Henderson settled matters, drilling home a half-cleared corner in a manner Gerrard would have been proud to call his own.
AC Milan 1-2 Liverpool — 2021 Champions League group stage
For the fourth time in four Champions League encounters, Milan found themselves in the lead against Liverpool, Tomori scoring at the right end on this occasion. For the third time in those four, they could not make it stick as Salah and the Reds' European cult hero Divock Origi made sure of the points.
