AC Milan vs. Inter: Ranking the tensest Derby della Madonnina matchups ahead of Champions League showdown

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The Derby della Madonnina, also known as the Milan Derby, is one of the most intense and historic rivalries in European football. AC Milan and Inter Milan have been battling it out since 1908, and with multiple trophies and titles between them, the stakes are always high when they meet.

With the two Milanese teams set to face each other in the Round of 16 of the Champions League this season, let’s take a look back at some of the most memorable, tensest and controversial encounters in their history.

1. 1965 European Cup Final

The 1965 European Cup Final is perhaps the most iconic Milan Derby in history. It was the first time that two teams from the same city had met in the final of Europe’s premier club competition. AC Milan started as slight favourites, but it was Inter Milan who emerged victorious, winning 1-0 with a goal from Jair.

2. 2005 Champions League Quarterfinals

The 2004/05 season was a special one for Liverpool, who went on to win the Champions League against all odds. One of the key moments of that campaign came in the quarterfinals, when they faced off against AC Milan. After a 3-2 win at Anfield, Liverpool were heavy underdogs when they travelled to the San Siro, but what followed was one of the greatest comebacks in Champions League history. Liverpool scored three goals in six minutes to level the tie and eventually won the trophy on penalties.

3. 2006 Coppa Italia Semifinals

The 2006 Coppa Italia Semifinals were a heated affair, with accusations of dirty play and unsporting behaviour on both sides. Inter Milan won the first leg 3-0, and AC Milan were left with a mountain to climb in the second leg. They came close, winning the game 2-1, but it wasn’t enough and Inter advanced to the final.

4. 2010 Champions League Quarterfinals

Another dramatic Champions League encounter between the two Milan clubs, the 2010 quarterfinals were a tense affair. Inter Milan were the reigning European champions, and AC Milan were determined to knock them off their perch. In the end, it was Inter who emerged victorious, with Wesley Sneijder and Maicon scoring the goals in a 2-1 win for the Nerazzurri.

5. 2021 Derby della Madonnina

The most recent edition of the Milan Derby was a thrilling encounter, with both sides playing attacking, high-energy football. Inter Milan took an early lead through a Romelu Lukaku penalty, but AC Milan fought back and equalised through Zlatan Ibrahimovic. The game ended in a 1-1 draw, with both sides having chances to win.

With so much history and passion between these two great clubs, the upcoming Champions League clash will no doubt be another memorable chapter in the story of the Milan Derby. Who will come out on top this time? Only time will tell.

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