Published By: Sayan Guha

UCL 2024/25: Real Madrid vs. AC Milan- The Night Madrid Crumbled in a 5-0 Rout at the San Siro

The rivalry between these two clubs is rooted in more than just trophies; it’s a story of mutual respect and the endless pursuit of excellence

As Real Madrid and AC Milan prepare for their Matchday 4 battle at Santiago Bernabeu on November 6th, the stakes are high. Madrid is currently 12th in the league table, while Milan looks to improve from 25th place. This game is a remembrance of Milan's historic 5-0 triumph against Madrid in the 1988–1989 European Cup semifinal. A packed San Siro watched Milan's masterpiece under Arrigo Sacchi as they stunned the Spanish giants and left an indelible stamp on football history.

The prelude to destruction

The first leg of the 1988/89 European Cup semi-finals at the Bernabeu was an exciting match. It seemed like Real Madrid was going to secure a narrow victory, but Milan's Van Basten made a stunning late equalizer with a header that silenced the Madrid supporters and set the stage for an intense second leg. Milan fans in Italy had a sense of destiny: could they defeat Madrid, who were nearly unbeatable on their home ground? Spoiler alert: they did, and the win was not even close.

The San Siro roars

From the start, Milan appeared to be on a mission. Carlo Ancelotti scored in style just 18 minutes into the encounter. With the ball at his feet, he dribbled past two Madrid players before blasting a long-range shot into the net. The stadium exploded, setting the tone for what would be one of the most memorable nights in Milan's history.

Rijkaard and Gullit strike

Shortly later, the Rossoneri increased their lead. In the 25th minute, Rijkaard headed the ball after Milan's great captain, Franco Baresi, sent it over from a corner kick. Madrid appeared shocked, but the worst was still to come.

Milan landed a third punch shortly before halftime. This time it was Ruud Gullit's turn. A well-timed cross from the irrepressible Donadoni found Gullit, who climbed above the Madrid defence to score 3-0. As the teams entered the locker room, Milan fans could sense that their club was doing more than just winning; they were making a message. Real Madrid had been dominated, and the San Siro was ablaze.

Van Basten joins the party

If Real Madrid expected to rebound in the second half, Milan had other intentions. Marco van Basten, the quiet assassin, got his name on the scoreboard only four minutes after the restart. Gullit's pass found Van Basten, who unleashed a thunderous left-footed shot that flew past Buyo. With that, it was 4-0, and Real Madrid was completely defeated. The overwhelming shock on the Madrid bench was palpable.

Donadoni’s decisive fifth

And just to finish the game, Roberto Donadoni stepped up one more. In the 60th minute, he received the ball on the edge of the box, dribbled past his man, and sent a crisp low effort past the Madrid custodian. 5-0! Madrid was left looking at the scoreboard, wondering how they'd been so completely destroyed, while Milan supporters were in heaven.

Milan accomplished the impossible, destroying Real Madrid and cementing their position in history. This encounter exemplified Milan's "Total Football" under Arrigo Sacchi, emphasising the perfect balance of tactics, skill, and determination. It remains the summit of European football.