The Best Moments at the San Siro, Milan’s Iconic Stadium at a Crossroads | OneFootball

One of the world’s most celebrated football stadiums could soon be lost, as Inter Milan and AC Milan have been approved to purchase the San Siro site and build a modern stadium next door, which would ultimately lead to the demolition of this historic venue.

The need for new stadiums is often tied to modern demands for comfort and safety. When Shea Stadium in New York City was replaced by Citi Field, the decision was clear: the old stadium, a relic of baseball’s 1960s expansion, no longer met contemporary standards. Similarly, River Plate’s iconic Monumental stadium in Buenos Aires has preserved its historic structure while implementing renovations over the last three years, adding seats, uniting sections, and bringing fans closer to the pitch by removing the running track.

The San Siro, a cathedral of soccer at its highest levels, is a mix of art and history, and its future now hangs in the balance after a city council vote approved the sale of the site to both Inter and AC Milan for €197 million.

The clubs plan to construct a 71,500-seat stadium adjacent to the current one, with the old San Siro replaced by parks, offices, and entertainment spaces. The proposal, submitted in March after previous delays, has the support of Milan’s mayor but faces opposition from some councillors, including Angelo Turco, who argue that the development plans are unclear.

Photos by Ignasi Torné Gualdo

Anyone visiting the San Siro would be hard-pressed to say it isn’t still capable of hosting top-tier events. Its architecture is instantly recognizable, dominated by massive cylindrical towers and bright red external ramps spiraling around the stadium, giving it a bold, industrial presence. Designed in the 1950s and expanded in the 1980s, the stadium combines functional engineering with striking visual impact. Open corners, steep stands, and layered tiers create an intimate and intense atmosphere, while the cantilevered roof protects spectators without obstructing views, making it both a sporting and architectural landmark.

Over the decades, the San Siro has hosted some of football’s most memorable events: three matches during the 1934 FIFA World Cup, the opening ceremony and six games of the 1990 World Cup, three matches at UEFA EURO 1980, and four European Cup finals in 1965, 1970, 2001, and 2016. Looking forward, it is set to host the opening ceremony of the 2026 Winter Olympics, shared between Milan and Cortina.

Beyond football, the San Siro has welcomed legendary musical acts, from Bob Marley and the Wailers to Michael Jackson, Pearl Jam, Taylor Swift, and The Weeknd. On and off the pitch, it has been the stage for some of the most unforgettable moments in sports and entertainment, solidifying its status as one of football’s true cathedrals.

So with the future of the stadium looking bleak, let’s look back at some of the most magical moments of the San Siro.

World Cup History

Photo by Bongarts/Getty Images

Perhaps the most iconic World Cup game at the San Siro came in 1934, when Italy defeated Austria 1–0 in the semifinals. Enrico Guaita scored the decisive goal, sending the Azzurri into the final where they would go on to win the first of their back-to-back World Cup titles.

When the tournament returned to Italy in 1990, the newly renovated San Siro hosted one of the greatest upsets in World Cup history. Defending champions Argentina, led by Diego Maradona, fell 1–0 to Cameroon after François Omam-Biyik’s unforgettable header. Maradona’s presence loomed over the tournament, especially after Argentina eliminated host nation Italy in the semifinals, sparking a backlash against him. Yet it was eventual champions West Germany who made the San Siro their fortress, winning four of their five matches in the stadium en route to lifting the trophy.

Countless Derbies

Photos by Ignasi Torné Gualdo

The Derby della Madonnina has defined San Siro for over a century. Since their first meeting in 1909, AC Milan and Inter Milan have clashed in countless dramatic encounters, with Inter holding the historical edge with 91 wins in 244 official matches.

One of the most infamous came during the 2005 Champions League quarterfinals. After a controversial refereeing decision, Inter supporters hurled flares onto the pitch, one striking Milan goalkeeper Dida. The match was abandoned, Milan awarded a 3–0 victory, and Inter handed heavy sanctions. Milan advanced but later suffered their famous collapse against Liverpool in Istanbul.

The derby has also produced wild scorelines, from Inter’s 6–5 comeback win in 1949 to Milan’s emphatic 6–0 triumph in 2001, the largest margin in the rivalry’s history. These clashes have made the San Siro one of football’s most dramatic stages.

European Nights

If San Siro is legendary for anything, it is the theater it has provided on European nights. In 1970, Feyenoord lifted their first European Cup there with a dramatic extra-time victory over Celtic. Tommy Gemmell had given Celtic the lead, but Rinus Israel equalized before Ove Kindvall sealed Feyenoord’s win in the dying moments.

In 2001, the Champions League final at San Siro saw Bayern Munich and Valencia battle to penalties. Oliver Kahn became the hero, saving Pellegrino’s spot-kick to hand Bayern their fourth European crown.

The stadium has also witnessed unforgettable semifinals, none bigger than Inter’s 3–1 win over Pep Guardiola’s Barcelona in 2010. Despite conceding early, goals from Wesley Sneijder, Maicon, and Diego Milito turned the tie, showcasing José Mourinho’s tactical mastery and cementing one of the all-time great San Siro nights.

Big Wins That Lead to Glory

Some domestic clashes at San Siro have carried title-winning significance. In 1989, with just five games remaining, Inter faced Maradona’s Napoli in a decisive Serie A showdown. Careca put Napoli ahead, but Inter responded through an own goal before Lothar Matthäus sealed victory with a stunning free kick. That win propelled Inter toward their 13th league title in a season defined by dominance.

For AC Milan, one of their greatest wins came against Real Madrid in the second leg of the 1989 European Cup semifinal. Milan’s 5-0 thrashing secured a 6-1 aggregate victory, with goals from Carlo Ancelotti, Marco van Basten, and future MLS star Roberto Donadoni.

Legacy of a Giant

Photo by Jonathan Moscrop/Getty Images

From World Cup drama and derby madness to European glory and title-deciding clashes, the San Siro has stood as one of football’s greatest arenas. To see it threatened by modern demands for luxury boxes and entertainment suites feels like the end of an era. Yet while the stadium may one day fall silent, the memories forged there will remain eternal.