There is a singular and curious aspect that makes Sunday night’s Milan - Napoli clash even more anticipated, and it concerns who sits on the bench. In fact, head coach Massimiliano Allegri and Antonio Conte will face each other again after 12 years: the last time was on October 6, 2013, Juventus - Milan 3-2 in favor of the ex Chelsea and Tottenham boss.
Previous encounters between Massimiliano Allegri and Antonio Conte:
The paradox is that two of the most successful coaches in Italian football history have not faced each other for so long, and in general, they have met only a few times. They faced each other only 8 times between November 2009 and October 2013.
The record clearly favors the coach of the ‘Azzurri’, who has 5 wins, all on Juventus’ bench and all against the Livorno-born coach on AC Milan’s bench. With the same teams, there were 2 draws, while Allegri’s only victory came in their first meeting when he coached Cagliari and Conte led Atalanta (3-0). There is a trend to reverse.
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11 out of 15: the Scudetto speaks their language:
And if we told you that at the time of their last face-to-face they had “only” won three Scudetti between them? One for Allegri on Milan’s bench and two for Conte on Juventus’. The rest is history: 11 of the last 15 championships were won by a team led by one of them.
Actually, Massimiliano Allegri added 5 more to his record with Juventus, while Conte added 3 with three different teams: Juventus, Inter, and Napoli. It will not be a personal duel, but the Livorno-born coach keeps a +1 in this sense, and who knows, this might also be a stimulus for the Salento coach.
So different, and yet so successful:
It is safe to think that fate wanted them to meet again after a Serie A start that suggests a possible duel between Milan and Napoli, separated by only 3 points. So far, together with Gian Piero Gasperini’s AS Roma side, they have been the most convincing teams. It is no coincidence that these two champions sit on the two benches.
One is calm and more composed (just don’t make him angry like in Milan - Bologna), the other more lively and meticulous. On one side, the media-reserved manager, on the other, the exuberant motivator who communicates dissatisfaction toward his club directly. To simplify: a manager versus a motivator, as pointed out by Milan Press.
The break after their last experiences at Juventus and Tottenham did them both good because they returned more charged and prepared than ever, ready to impress themselves and critics. Incredibly, their paths could have been opposite: if only AC Milan had bet on Antonio Conte in summer 2024, if only Napoli had gone for Massimiliano Allegri in summer 2025.
What did legendary ex Juventus and Milan coach Fabio Capello say about the much-anticipated encounter?
“On one side, Allegri has brought balance, because now when the Rossoneri lose the ball, the team no longer looks split, leaving the field open to counterattacks,” he told Gazzetta dello Sport. “Not by chance, in five out of six matches this season, they have not conceded. On the other side, he has quality players capable of possession both horizontally and vertically, both conservatively, when he wants to control the game, and offensively, if there is a need and chance to hurt the opponent. Max against Antonio, the two best managers in Italy today: it will be a super match. Allegri has won more league titles than anyone in the current Serie A, while Conte has also managed to win the Premier League. I was always taught that the best win, so..."
Now, on Sunday at San Siro, they want to wip out every "if" and "but": the kings of Italian football are them, and they have proven it over the last 15 years, but the throne belongs to only one.
