The 3 Greatest Derby Della Madonnina of All-Time

The Derby della Madonnina, also known as the Milan Derby, is one of football's most storied and passionate rivalries. When AC Milan and Inter Milan meet, it’s about more than just points or bragging rights—it's about pride, history, and the fierce competition between two clubs that share a stadium but are worlds apart in terms of identity and culture.

This clash has given us countless unforgettable moments, but a few stand out as the greatest in the derby's illustrious history. With AC Milan and Inter Milan facing off against each other later in the weekend, we decided to take a look at some of the greatest Milan derbies of all-time. 

1) AC Milan 6-0 Inter Milan (May 2001) – The Rossoneri’s Ultimate Triumph 

Football derbies are always intense. Even when a team is struggling, they often find an extra gear when it comes to facing their city rivals. But no one expected the utter demolition that AC Milan handed Inter in May 2001. The 6-0 scoreline is one of the biggest in the history of the Derby della Madonnina, and it’s still a source of immense pride for Milan fans and painful memories for Inter. Going into the match, both teams were having relatively underwhelming seasons by their lofty standards. Milan had parted ways with their coach Alberto Zaccheroni, while Inter had been inconsistent all year. Despite this, derbies always carry a weight of expectation, and few could have predicted the onslaught that was about to unfold. 

From the first whistle, AC Milan played like a team possessed. Within 20 minutes, Gianni Comandini—who was not exactly a household name—had already put Milan 2-0 up. Inter’s defense looked in shambles, unable to cope with Milan’s relentless pressure and attacking fluency. Andriy Shevchenko, Milan’s star striker, made matters worse for Inter by scoring twice, showing why he was considered one of the best forwards in the world at the time. Serginho and Federico Giunti added to the carnage with a goal each, and the scoreline became a symbol of Milan’s total dominance. 

The beauty of this victory wasn’t just in the goals. It was in how AC Milan systematically dismantled their biggest rivals. Every pass, every run, every tackle was made with precision and intent. Inter’s defense, which had been fairly reliable throughout the season, looked completely out of its depth. The final whistle blew, and Milan had not only secured a comprehensive victory but had also made a statement about their dominance in the city. To this day, the 6-0 victory remains one of the biggest and most satisfying wins in AC Milan’s history, a game forever etched in the hearts of their supporters. 

2) Inter Milan 4-2 AC Milan (February 2020) – A Tale of Two Halves  

Fast forward nearly two decades, and we arrive at a derby that, though not as lopsided, was every bit as dramatic and memorable. In February 2020, Inter Milan pulled off one of the most thrilling comebacks in Derby della Madonnina history, beating AC Milan 4-2 after being 2-0 down at halftime. This was a game that had everything—goals, tension, high-quality football, and the kind of emotional rollercoaster only a derby can deliver. 

AC Milan, led by Zlatan Ibrahimović, came out of the blocks fast. Ibrahimović, always one for the big occasion, was involved in everything. He provided the assist for Ante Rebić’s opening goal and then added a second with a header just before halftime. At that point, Milan looked in control. They had dominated the first half and Inter seemed to have no answers. But Inter manager Antonio Conte must have delivered an incredible halftime team talk, because the second half was a different story entirely. Inter came out with renewed energy and determination, and within minutes they were back in the game. Marcelo Brozović scored a stunning volley from outside the box, a goal that seemed to spark life back into the Nerazzurri. 

Just moments later, Matías Vecino equalized, finishing off a well-worked team move to make it 2-2. The momentum had completely shifted, and Milan looked shell-shocked. Inter pressed forward relentlessly, and it was only a matter of time before they took the lead. That moment came in the 70th minute, when defender Stefan de Vrij headed in a corner to put Inter 3-2 up. The San Siro erupted as the blue half of the stadium sensed victory. 

In the dying minutes, as AC Milan pushed forward in search of an equalizer, Romelu Lukaku sealed the win with a towering header in stoppage time. The comeback was complete and Inter had pulled off one of the most memorable victories in recent derby history. This match wasn’t just about the goals—it was about the sheer drama of it all. Inter looked dead and buried at halftime, only to come roaring back in a display of resilience and attacking brilliance. For AC Milan, it was a harsh reminder of the fine margins in football. And for Inter, it was a triumph that kept them firmly in the hunt for the Serie A title. 

3) Inter Milan 0 – 1 AC Milan (April 2005) -- The Birth of One of the Most Iconic Photos 

Going into the 2nd leg, AC Milan held a commanding 2-0 lead over their city rivals. A brace from Andriy Shevchenko had turned the tie in Milan’s favor. However, Inter were keen to wrestle back the control of the tie. And with Inter being designated as the home side in the second leg, the Nerazzurri ultras were in full voice. But what transpired in the next 90 minutes was Derby della Madonnina at its best, but also at its worst. Inter needed a spark to overturn the two-goal deficit. But their hopes were dashed early on when Shevchenko once again found the back of the net, giving Milan a 3-0 lead on aggregate. The tie looked all but over, and frustration began to seep through the Inter ranks and into the stands. 

The pivotal moment of the match came in the 72nd minute when Inter thought they had scored through Esteban Cambiasso, only for the goal to be disallowed. What followed was one of the most infamous scenes in Champions League history. Flares rained down from the stands, with one hitting Milan goalkeeper Dida. Chaos erupted, and the match was suspended as officials tried to restore order. But the crowd was relentless, and after a 20-minute delay, the game was abandoned altogether. 

Amidst the chaos, an iconic image emerged: AC Milan’s Rui Costa, calmly standing next to Inter’s Marco Materazzi, both watching the unfolding mayhem as flares lit up the night sky. That moment encapsulated the surreal atmosphere—two fierce rivals united by disbelief at what was happening around them. Ultimately, UEFA awarded AC Milan the victory, securing their place in the semi-finals. It was a night remembered not just for Milan’s dominance but for the way football took a backseat to chaos. The iconic image of Rui Costa and Materazzi remains a symbol of that infamous night, where passion and frustration spilled over in one of the world’s greatest derbies.      

Also Read: Inter Milan vs AC Milan – Serie A – Preview, Team News and Updates