3 Memorable Clashes Between AC Milan and Liverpool on the European Stage

Few matchups in European football carry the same weight of history, drama, and sheer unpredictability as AC Milan vs. Liverpool. These two European giants have crossed paths on several high-stakes occasions, creating some of the most unforgettable moments in Champions League history.

When you think of AC Milan and Liverpool, you think of two clubs rich in tradition, success, and passionate fanbases that bring their A-game when the stakes are highest. But it’s the encounters between them on the biggest stage—Europe—that have etched themselves into football folklore. With the football gods deciding to pit these two European champions against each other in the first gameweek of the revamped Champions League, we decided to dive into three of the most memorable AC Milan vs. Liverpool clashes that have given fans across the globe unforgettable memories. 

1) The Miracle of Istanbul – 2005 UEFA Champions League Final 

You can’t talk about AC Milan and Liverpool without immediately thinking of one of the greatest football matches of all time: the 2005 Champions League final in Istanbul. Even if you’re not a Liverpool fan, chances are you’ve heard the legendary tale of that night. 

On May 25, 2005, at the Atatürk Olympic Stadium, Milan were at the peak of their powers. Carlo Ancelotti's men were stacked with some of the world’s best: Andriy Shevchenko, Paolo Maldini, Kaká, Andrea Pirlo, Clarence Seedorf—the list goes on. They were the overwhelming favorites to win, and for good reason. Within the first minute, Milan had already stamped their authority on the match, as captain Paolo Maldini volleyed the ball home from a Pirlo freekick. A blistering first half saw Milan race to a 3-0 lead by halftime, thanks to a double from Hernán Crespo. Game over, right? Not quite. 

As the Milan fans sang in celebration, and Liverpool supporters feared the worst, something clicked in the minds of the Reds during the halftime break. Rafa Benítez’s team came out for the second half with renewed spirit, and within 15 minutes, they pulled off one of the greatest comebacks in the history of sports. It all started with a Steven Gerrard header in the 54th minute, followed by a goal from Vladimír Šmicer just two minutes later. Suddenly, the game was on. By the 60th minute, Liverpool had leveled the score when Xabi Alonso scored from the rebound of his own saved penalty. The impossible had happened: Liverpool, 3-0 down, were now tied 3-3 with AC Milan. 

Extra time couldn’t separate the two sides, but the most dramatic chapter was yet to come. In the penalty shootout, Liverpool's goalkeeper Jerzy Dudek performed heroics, saving efforts from Pirlo and Shevchenko. Liverpool won 3-2 on penalties, completing one of the most astonishing comebacks in football history.  

2) The Revenge of Athens – 2007 UEFA Champions League Final 

Two years after the Miracle of Istanbul, Milan had a chance to avenge their heartbreaking loss, and they got their shot in the 2007 UEFA Champions League final in Athens. The storyline couldn’t have been more perfect—a rematch between two clubs with unfinished business on the grandest stage. 

This time, Milan were determined not to let history repeat itself. While Liverpool still had their core group of players like Steven Gerrard and Jamie Carragher, Milan entered the match with a clear focus and a desire to set the record straight. Once again, Carlo Ancelotti was at the helm, and this Milan side was just as strong—featuring Kaká, Pirlo, Gennaro Gattuso, and Filippo Inzaghi. 

From the outset, Milan played a much more cautious game compared to their all-guns-blazing approach in 2005. This was a tactical masterclass from Ancelotti. Milan allowed Liverpool possession but soaked up the pressure, biding their time to strike. That moment came just before halftime when Andrea Pirlo's freekick took a fortunate deflection off Filippo Inzaghi, wrong-footing the Liverpool defense and Dudek’s replacement, Pepe Reina. Inzaghi was the difference maker once again. Despite the scrappy nature of the goal, it was enough to unsettle Liverpool and tilt the game in Milan’s favor. 

In the second half, Liverpool tried to push for an equalizer, but they couldn't find a way past a resilient Milan defense. Then, in the 82nd minute, Kaká—who was in the form of his life that season—slipped a beautifully weighted pass through to Inzaghi, who rounded Reina and slotted home Milan’s second goal. It was game, set, and match. And this time, there would be no Liverpool comeback. Dirk Kuyt pulled one back for Liverpool in the 89th minute, but it was too little too late. Milan held on to win 2-1, securing their seventh European Cup and getting their sweet revenge for Istanbul. It wasn’t the same dramatic spectacle as 2005, but for Milan fans, it was every bit as satisfying. 

3) Group Stage Thriller – 2021 UEFA Champions League Group Stage 

After more than a decade since their last European clash, Milan and Liverpool were once again drawn together in the 2021/22 UEFA Champions League group stage. This wasn’t a final or even a knockout round, but the sense of history was palpable as the two clubs met at Anfield in September 2021. Both sides had undergone significant transformations since their legendary encounters in the 2000s. Liverpool, under Jürgen Klopp, had become one of Europe’s top teams again, winning the Champions League in 2019 and the Premier League in 2020. Milan, after years of struggles, were finally back on the top step of European football under Stefano Pioli, eager to reestablish themselves among Europe’s elite. 

This match had all the hallmarks of a classic, and it didn’t disappoint. Liverpool started the game in blistering fashion, and it seemed like Milan were in for a long night. Trent Alexander-Arnold’s marauding run led to the first goal in the ninth minute, as his shot deflected off Milan defender Fikayo Tomori into the net. When Mohamed Salah had a penalty saved by Mike Maignan shortly after, it looked like Liverpool would dominate the game. 

But Milan had other ideas. In a two-minute flurry before halftime, they stunned the Anfield crowd with two quick goals. First, Ante Rebić slotted home from a clever Rafael Leão pass, and just moments later, Brahim Díaz tapped in after a goalmouth scramble. Out of nowhere, Milan were leading 2-1, and it felt like a throwback to those dramatic Milan-Liverpool clashes of the past. 

Liverpool, though, showed their resilience in the second half. Salah made amends for his penalty miss by equalizing in the 49th minute, and Jordan Henderson’s thunderous half-volley in the 69th minute gave Liverpool a 3-2 lead. It was a captain’s goal in every sense—Henderson had stepped up when his team needed him most. Milan pushed for an equalizer, but Liverpool held firm, securing a thrilling 3-2 win in front of a raucous Anfield crowd. It may not have been a Champions League final, but this match encapsulated everything that makes European nights special. Two teams with rich histories going toe-to-toe, producing high-quality football and unforgettable moments. 

Also Read: AC Milan vs Liverpool – UEFA Champions League – Preview, Team News and Updates