Milan – Napoli: Reliving the memories of a Scudetto race

28/09/2025 08:32:00 TrophyTracker

As the weekend draws near and the Milan - Napoli match is just steps away, memories of past Scudetto battles between them hurriedly return…

1. This is only the 5th round of Serie A, too early to talk about a Scudetto race between them or to assess Milan’s revival under coach Max Allegri. Milan currently ranks third, trailing Napoli by 3 points; the Scudetto journey is still long ahead, but memories of their championship contests remain eternal.

They once contested the Scudetto in the late 1980s and early 1990s, during the time when Milan was led by president Silvio Berlusconi and Napoli by Corrado Ferlaino, both now deceased. In 1988, Milan versus Napoli was a clash between 1987 Ballon d’Or winner Ruud Gullit and the brightest contemporary star Diego Armando Maradona; emerging striker Marco van Basten challenging the famed South American marksman Antonio Careca; a rising force playing revolutionary football challenging the dominance of southern Italy’s club.

Before the first leg of the 1987/88 season, Napoli led the table by 5 points over Milan in fourth place (back then, wins counted for 2 points). Maradona assisted Careca to open the score, silencing 80,000 Milan fans at San Siro, but that was all Napoli achieved that day. The golden-haired angel Angelo Colombo equalized at 1-1. Carlo Ancelotti passed to Pietro Virdis for another goal. Gullit thrilled San Siro with a run past three defenders and the Napoli goalkeeper to score the third, the best goal of the match. Roberto Donadoni sealed a beautiful 4-1 win for Milan after a pass from Ancelotti. A true race had started.

Four months later, on May 1, 1988, with only 3 rounds remaining and the teams level on points, a real final took place at the stadium then called San Paolo. Maradona shone again, scoring first, but it was not enough, because in the duel of the two number 10s that day, Gullit was superior with two assists to Virdis and Van Basten, defeating Napoli 3-2. Milan went on to win the Scudetto.

Modric versus De Bruyne rekindles memories of the Gullit-Maradona duel nearly 40 years ago

2. Nearly four decades later, who will take on the roles of Gullit (still strong at 63) and Maradona (now in the sky) when Milan challenges Napoli’s power, the reigning champions as before? Luka Modric, also a Ballon d’Or winner, and Kevin De Bruyne, among the brightest stars of his generation, are visible candidates. Although neither wears the number 10 like Gullit and Maradona did (Modric wears 14, De Bruyne 11), they have clearly influenced the styles of Milan and Napoli from their first appearances. Modric is the conductor of Milan’s symphony with his passes, threading balls, and controlling the game’s rhythm. De Bruyne supports defense, distributes the ball, organizes attacks, and takes set pieces, much like Maradona did in his Napoli days.

Modric and De Bruyne have met several times in top Champions League matches with Real Madrid and Man City. Now, they bring that atmosphere and quality to this stage, lighting up Serie A stadiums and stirring the hearts of millions of fans. They lead their younger teammates in a new battle where Milan does not want to repeat last season’s two losses, aiming to declare their readiness for the Scudetto race after a failed season, with four consecutive wins as the best preparation for their first big match of the season. Milan - Napoli is also a duel between Max Allegri and Antonio Conte, two of Serie A’s best coaches, who together have won 11 Scudetti. This will be their first meeting on the field since Conte’s Juventus defeated Allegri’s Milan 3-2 almost 12 years ago. Surprisingly, they have only faced each other five times in Serie A, with Conte winning four and Allegri one.

Much will change after Sunday night if there is a decisive result. Either Napoli continues to dominate Serie A as they currently do, or Milan’s power revival under Allegri creates a new rival in the Scudetto race. The answer will come soon, on a night when San Siro dreams of returning to the glory days, with the towering Gullit and the elegant Van Basten…

Anh Ngọc

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