© Imago
Head-to-head record
Previous meetings: 5
AC Milan wins: 1
Draws: 0
Liverpool wins: 4
A match that is forever etched into the annals of the Champions League, Milan and Liverpool may have only met on five previous occasions in competitive action, but their inaugural meeting provided one of the most unforgettable nights the tournament has ever seen.
Nothing more can be said about the 2005 Miracle of Istanbul that has not already been said, as Rafael Benitez's Liverpool pulled off the improbable by fighting back from three goals down to take that year's Champions League final to the unlikeliest of penalty shootouts.
Up steps Jerzy Dudek, who after producing a magnificent double save from Andriy Shevchenko in extra time also denied the Ukrainian and Andrea Pirlo from the penalty shootout; cue the scenes of Steven Gerrard hoisting the famous trophy aloft.
A miffed Milan avenged that agonising defeat two years later, though, when Filippo Inzaghi was at the double in the 2006-07 Champions League final to secure Milan's seventh and most recent triumph in the competition; Dirk Kuyt's effort was a mere consolation in Athens.
After locking horns twice in finals in the space of three years, Liverpool and Milan had to wait another 14 years to cross paths again in the Champions League, and in keeping with Reds-Rossoneri tradition, their September 2021 showdown was a thriller.
In front of the Kop, Liverpool emerged victorious by a 3-2 scoreline as Jordan Henderson's 69th-minute drive settled a gripping group-stage showdown, where Brahim Diaz, Ante Rebic, Mohamed Salah and Fikayo Tomori - in the wrong goal - also registered.
Liverpool made it two for two at San Siro a couple of months later, thanks to another effort from the timeless Salah and favourite son Divock Origi, who is now out in the cold at AC Milan after being banished from the first team.
That 2-1 triumph was actually Liverpool's second of three straight wins at Milan's home - they have also defeated Inter Milan away from home twice in 2008 and 2022 - meaning that the Reds are the only team to visit San Siro more than once in the Champions League and hold a 100% record.
That San Siro sequence became four in September 2024, when Liverpool boss Arne Slot and his Milan counterpart Paulo Fonseca each took charge of their first Champions League matches for their respective clubs, and it was the Merseyside giants who fought back from a goal down to win 3-1.
Previous meetings
Sep 17, 2024: AC Milan 1-3 Liverpool (Champions League League Phase)
Dec 07, 2021: AC Milan 1-2 Liverpool (Champions League Group Stage)
Sep 15, 2021: Liverpool 3-2 AC Milan (Champions League Group Stage)
May 23, 2007: AC Milan 2-1 Liverpool (Champions League Final)
May 25, 2005: AC Milan 3-3 Liverpool(p) (Champions League Final)
Ben Knapton
