A look back at the Greatest matches between Liverpool and AC Milan
By Luke Birch
The Reds first game in the new Champions League format will be against familiar foes on Tuesday night.
Liverpool will face off against AC Milan for the fifth time in history.
Buckle-in as we countdown Liverpool’s four previous clashes against the Rossoneri, and there are some mammoth ones in there.
4. AC Milan 2-1 Liverpool (2007)
A game that is often used by many to signify the end of Rafa Benitez’s glory years at Liverpool.
The Reds travelled to Athens to play AC Milan in the 2007 Champions League final.
Having dispatched Barcelona in the Round of 16, and Chelsea for the second time in three seasons in the semi-final, the Reds were on course to win another European Cup against AC Milan in the final.
Filippo Inzaghi provided the goalward touch from an Andrea Pirlo free-kick to give AC Milan the lead.
Kaka fed Inzaghi through for his second, tucking underneath Pepe Reina, and running over to the corner flag to celebrate.
Late-on, Jermaine Pennant’s corner was flicked on by Daniel Agger who found Dirk Kuyt to head home a Liverpool consolation at the back-post.
3. AC Milan 1-2 Liverpool (2021)
The first-ever match between these two European heavyweights to be played at the San Siro.
Having already guaranteed their progression to the knockout stages, Liverpool were under little pressure in their matchday six group stage tie against AC Milan.
Alessio Romagnoli’s header was parried by Alisson, only for former Chelsea defender Fikayo Tomori to capitalise and give the Rossoneri the lead.
Five minutes later, Alex Oxlade-Chamberlain wriggled his way through the Milan midfield, his shot saved by Mike Maignan, before Mo Salah slotted home the rebound.
Tomori had the ball stolen by Sadio Mane before future Milan forward Divock Origi headed-in.
This victory saw Liverpool become the first English team to win all six Champions League group games.
2. Liverpool 3-2 AC Milan (2021)
This was the first meeting between the teams since 2007, and the first European night back at Anfield after Covid-19 lockdowns, and what an occasion it turned out to be.
Liverpool made their early dominance count, when Trent Alexander-Arnold had his effort deflected off Fikayo Tomori and into the net.
The hosts soon found themselves frustrated when Mo Salah’s penalty was saved by Mike Maignan.
Rafael Leao rolled the ball through for Ante Rebic for AC Milan to equalise against the run of play.
Liverpool found themselves again on the receiving end of Milan goal on the stroke of half-time, when Brahim Diaz followed the ball-in from an Andy Robertson block to give the visitors a surprise half-time lead.
Divock Origi chipped the ball over the top of the Milan defence for Salah to poke home early in the second-half.
Alexander-Arnold’s free-kick was cleared away by the Milan defence, before Jordan Henderson steamed onto the ball to drill home first-time from the edge of the area.
Liverpool completed the outstanding comeback to the soundtrack of a raucous Anfield, on one of its great European nights.
1. AC Milan 3-3 Liverpool (2-3p) (2005)
Perhaps the greatest night in Liverpool’s history.
The road to the 2005 Champions League Final was a memorable one. What began on a wing and a prayer in the third qualifying round against Austrian club Grazer AK, blossomed into a triumph for the ages.
Steven Gerrard (and Neil Mellor’s) heroics against Olympiacos saved Liverpool from a premature exit in the group stage.
An emotional night against Juventus saw Liverpool advance thanks to more heroics, this time from Sami Hyypia and Luis Garcia.
Then in the semi-final second leg, Luis Garcia’s ‘ghost goal’, saw Liverpool edge out Chelsea, soundtracked by arguably Anfield’s greatest-ever atmosphere.
Istanbul came. Milan were the greatest team in the world, and they showed it early-on.
It was a blur. Paolo Maldini volleyed home inside a minute, Andriy Shevchenko found Hernan Crespo for two, Crespo again, 3, and the dream went up in flames in front of the eyes of the world.
Something happened at half-time.
Liverpool lifted, John Arne Riise lifted it for Steven Gerrard, “Hello, hello, here we go”.
And they went.
In his last appearance in a red shirt, the ageing Vladimir Smicer sliced home two, at 3-2, Red shirts were flying everywhere, Baros laid it off as Gerrard’s shirt was tugged back by Genaro Gattuso.
Then there was silence. Xabi Alonso strode up to the spot tentatively, like having a kickabout with the kids on a Sunday morning. Saved by Dida. Xabi ALONSO! 3-0 down five minutes ago. Now equals.
Lest we never forget Jerzy Dudek’s double save from Shevchenko, the real miracle, thus it went to penalties at 3-3.
Shevchenko had to score. Had to score. Couldn’t eye Dudek who had defied everything to deny him before.
Dudek committed to his right-hand corner, but Shevchenko had chipped it down the middle, stretching, straining, Dudek batted it away.
Liverpool broke a 21-year duck, Champions of Europe. Keep it forever.
In Istanbul we won it five times.
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