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When the 2022/23 UEFA Champions League campaign got underway, we highly doubt that anyone would have predicted an all-Milanese semifinal. But following AC Mian’s upset victory against runaway Serie A leaders Napoli and Inter Milan holding their nerve to dispatch Benfica, that is exactly what we are about to witness. And it isn’t the first time.
Exactly 20 years ago, the Rossoneri and the Nerazzurri squared off for a spot in the Old Trafford-hosted Champions League final. Back then, however, Serie A was a much more competitive league, and so seeing the two sides reach the latter stages of European football’s most elite competition wasn’t anywhere near as surprising as it is today. With the likes of Kaka, Andriy Shevchenko, Hernán Crespo, and Christian Vieri on display, both squads were stacked with talent.
Two decades on from Italian football’s heyday and Serie A is lagging the rest of Europe somewhat. Despite both Milan clubs and Serie, A itself garnering extra income from partnerships with different betting websites. The partnerships have allowed their fans to enjoy the thrill of playing in an online casino for real money but they haven’t catapulted the Italian top flight back into the limelight, until now.
There is nothing that ignites football fans’ passion and excitement quite like a derby match, especially with the highest of stakes. And when it comes to fierce derbies in Italy, nothing compares to the Milan Derby, pitting two of the country’s most successful and supported teams against each other. Both AC Milan and Inter Milan have a long-standing rivalry on and off the pitch, and arguably the most memorable moment in the historic rivalry was their semifinal clash two decades ago.
Road to the semifinal
The two Milanese clubs had to fight tooth and nail before they could face off against each other in the semifinals. Back then, the Champions League had two group stages rather than one, meaning that the run to the latter stages was a test of endurance as well as ability. AC Milan finished top of their initial group, with four wins, one draw, and one loss, beating the likes of Deportivo La Coruna, Lens, and Bayern Munich along the way. In the second group phases, they would once again top their group, finishing ahead of Real Madrid, Borussia Dortmund, and Lokomotiv Moscow, setting up a quarterfinal against Ajax.
In that two-legged last-eight tussle against the Dutch giants, they had to fight like champions. In the latter stages of the second leg, the score was level at two apiece. As the first leg in Amsterdam finished goalless, Ajax would progress on away goals if the hosts couldn’t find a winner at the San Siro. In the 91st minute however, Danish striker Jon Dahl Tomasson popped up with a last-gasp winner to send the Rossoneri through to the semifinals.
Inter also topped their initial group en route to the knockout stages. They progressed ahead of Ajax, before finishing as runners-up to Barcelona in the second group stage. They then defeated would-be Spanish Champions Valencia in the quarterfinals to set up a mouth-watering semifinal against their city rivals.
AC Milan progress on away goals
The first leg of the semifinal took place on April 23, 2003. Despite the two clubs both calling the San Siro their home, AC Milan were the designated home team in the first leg, while the Nerrazzurril would return the favor the following week. But just as was the case in the Rossoneri’s first leg in the previous round, the match would end goalless.
In the second leg, Milan looked to have one foot in the final when Andriy Shevchenko gave his side the lead in the stroke of halftime. The visitors managed to hang onto their lead until the latter stages when Obafemi Martins found a late equalizer. Courtesy of the away goals rule, the hosts knew they needed another goal, but that goal never came, and it was Milan who progressed to the final.
In the Old Trafford final, the Rossoneri met another set of Italians in the form of Juventus. And following 120 goalless minutes, the tie would head to a penalty shootout, it was Milan who would eventually prevail courtesy of heroics from Brazilian goalkeeper Dida.
The years since
After that triumph against the Bianconeri, Milan went through a series of highs and lows. They memorably lost the 2005 Champions League final to Liverpool, with the Reds coming back from three goals down to secure a 3-3 draw and eventually win on penalties. Milan would have their revenge two years later however, defeating the same team in Athens courtesy of a Flippo Inzaghi double and securing the famous ‘Big Eared’ trophy for the seventh time. Inter meanwhile would need to wait until 2010 for their time to come. And the iconic Portuguese manager Jose Mourinho was the man who brought success. The current Roma boss led the Nerrazzurri to an unprecedented treble that year, with a Diego Milito double in the Santiago Bernabeu securing the UEFA Champions League for just the third time in the club’s illustrious history.
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