Napoli v Milan: Conte v Allegri, clash of Italy’s top bosses | OneFootball

Napoli v Milan: Conte v Allegri, clash of Italy’s top bosses | OneFootball

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·18 December 2025

Napoli v Milan: Conte v Allegri, clash of Italy’s top bosses

Article image:Napoli v Milan: Conte v Allegri, clash of Italy’s top bosses

The Italian Super Cup semifinal between Napoli and Milan is worth more than just a spot in the final. The night in Riyadh becomes the stage for a clash that goes beyond the pitch, transforming into yet another chapter of a rivalry that has deeply marked the recent history of Serie A.

Napoli-Milan, Conte vs Allegri: the showdown between the dominators of Italian football

Napoli-Milan is above all Antonio Conte against Massimiliano Allegri, two coaches who, between 2011 and 2020, exercised a true duopoly over Italian football.


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Conte and Allegri, the “masters” of an era

For almost a decade, Conte and Allegri shared power in Serie A, winning a total of nine consecutive league titles. A dominance interrupted only in more recent times by coaches like Sarri, Pioli, Spalletti, and Inzaghi, but which has not diminished the prestige and aura of greatness that still surrounds the two managers today.

Napoli-Milan, scheduled for this evening at 8:00 PM live on Italia 1 and Sportmediaset.it, brings back to center stage two different but equally successful philosophies, embodied by coaches who have made mentality and group control their trademark.

Previous encounters: numbers favor Conte, but Allegri struck last

Despite years of parallel dominance, direct clashes between Conte and Allegri have been less frequent than expected. In total, there have been just nine official meetings. The record favors the coach from Salento, who has achieved five victories, compared to two draws and two wins for Allegri.

The last encounter, however, smiled on the coach from Livorno: Allegri’s Milan defeated Conte’s Napoli in the league last September 28, a result that adds further tension and significance to the Super Cup semifinal.

That curious crossing in Doha and a rivalry that never exploded in the Super Cup

Paradoxically, Conte and Allegri have never faced each other directly in an Italian Super Cup final. Yet, their paths crossed in an emblematic way in the 2014 edition in Doha.

On that occasion, Napoli won the trophy by beating Allegri’s Juventus on penalties. However, that Juventus had reached the final thanks to the record-breaking 102-point league title won by Conte just a few months earlier, before his sensational summer departure. An ideal passing of the torch that makes tonight’s clash even more symbolic.

The relationship with the Super Cup: Conte chasing his sixth triumph

Massimiliano Allegri is universally recognized as a specialist in one-off matches and finals. In his career, he has already won three Italian Super Cups, one with Milan and two with Juventus, confirming a particular aptitude for this type of competition.

Antonio Conte, however, is no less. His bond with the Super Cup is deep and rooted in a winning DNA that has never left the Apulian coach. In total, Conte has lifted this trophy five times: three as a player and two as a coach. Tonight, in Riyadh, he is chasing his sixth personal title, fully aware that the past grants no advantages.

Napoli-Milan thus presents itself as a match full of history, prestige, and meaning. A game that can change the momentum of the season and that, once again, puts two symbolic coaches of modern Italian football face to face. Conte against Allegri, with no compromises.

This article was translated into English by Artificial Intelligence. You can read the original version in 🇮🇹 here.

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