Napoli against Milan down the years has often been a battle of superstars.

Rewind to their titanic clashes at the end of the 1980s and the memories of Diego Maradona against Ruud Gullit: Careca vs Marco van Basten; Alemao slugging it out with Carlo Ancelotti in midfield. A time when calcio ruled the world.

Fast forward to the beginning of the 2010s, and you had Edinson Cavani against Zlatan Ibrahimovic; Marek Hamsik vs Andrea Pirlo; Clarence Seedorf squaring off with Gokhan Inler.

As the champions Napoli travel north to face Milan at San Siro, the two superstars on display will be the managers.

Antonio Conte and Max Allegri have not sat in opposing dugouts for 12 years, when Allegri was in the final throes of his first stint on the Milan bench and Conte was in the process of laying the groundwork for Juventus’ unprecedented domination of the Italian game.

That last meeting, in October 2013, was won by Conte, with Juve coming from a goal down to win 3-2 at the Allianz Stadium.

Among the scorers that day were Pirlo and Giorgio Chiellini, and while Conte does not have anywhere near the same kind of quality in his modern Napoli side, the Puglia native has undoubtedly improved since his early days.

Conte and Allegri are the finest Italian coaches of their generation, between them they have won 11 league titles. The other 18 coaches in Serie A have two combined.

Allegri and Conte are serial winners, yet fate has made it that they rarely cross swords.

Sacked by Milan in January 2014 as the ‘banter years’ were about to be put in motion, Allegri replaced Conte in Turin six months later after the Juve legend walked out of the club in disgust over transfer strategy. 

Allegri’s car was pelted with eggs and spat on as he arrived at Juve’s headquarters for his unveiling in those stormy days in July 2014. Many Juventini believed he was the wrong man for the job, with his Milan sacking still fresh in the memory.

Yet Allegri arguably did a far better job with Juve than Conte did. He took what was ostensibly the same squad of players, bar an unknown Kingsley Coman, Alvaro Morata and an ageing Patrice Evra, to within 90 minutes of winning a treble in his first season.

The domination that Conte started with Juve intensified under Allegri: he would go on to win four league and cup doubles from 2015 to 2019 and take the Bianconeri to two Champions League finals.

After Juve, Conte wouldn’t find himself in Serie A again for a further five years, rocking up at Inter the same summer Allegri departed Juve and, inevitably, led the Nerazzurri to their first league title since 2010 and in the process being the one to halt the Juve domination he started.

Allegri then returned to Serie A as Conte once again exited stage left after becoming disgruntled with Inter’s finances and lack of ambition.

Three years later, Conte returned just as Allegri was on the receiving end of his second sacking from Juve, and the Tuscan’s sabbatical coincided with Conte steering Napoli to an unlikely Scudetto, becoming the first manager to win the title in Italy with three different clubs.

Now, finally, both are back in the league at the same time, and Sunday night’s meeting between the two most successful coaches in modern Serie A history adds gravitas to what is already an important fixture.

Neapolitans don’t loathe Milan to the same extent as Juventus, but they still represent northern arrogance.

Battles between the two have often been framed around the theme of northern superiority against southern pride. This was heightened during the Maradona years when the upstart from Villa Fiorito galvanised Napoli, and a city, to consistently topple Milan, Inter and Juve in the second half of the 1980s.

Conte has weaponised Neapolitans’ unparalleled passion for the club since arriving, with Napoli’s average attendance last season higher than even the 2022-23 title-winning campaign.

Supporters have taken to Conte, knowing that despite the black-and-white blood that courses through his veins, he is changing the mentality of the club. Conte could be the first coach in Napoli’s history to retain the title.

Allegri, by contrast, has been brought in to restore order at Milanello. Last season Milan’s trainwreck mirrored Napoli’s 2023-24, and while Aurelio De Laurentiis turned to Conte to set things right, RedBird wanted Allegri to kickstart a major reset.

At this stage of his career Allegri is, if anything, a safe pair of hands, a coach good enough to secure a top-four spot, the minimum objective.

And so far, so good. He has got Milan scoring goals, with six in the last two games between the league and Coppa Italia. There has been little of the anti-football we saw for three years at Juventus.

Conte has been applauded for his adaptability since arriving in Naples, rarely digging into his pocket to utilise the 3-5-2 he implemented with distinction at Juve, Inter and with Italy.

He shifted to a 4-3-3 to maximise Scott McTominay’s arrival, and now this season has switched again to a 4-1-4-1 to make use of Kevin De Bruyne and due to Romelu Lukaku’s injury.

Yet if Conte has changed, so has Allegri. Always a pragmatist and ready to tailor his system to the players at his disposal, he’s adapted a 4-3-3 formation in Milan, brought Ruben Loftus-Cheek in from the cold, and they look good even without star player Rafael Leao, out through injury.

Like Napoli last season, Milan playing once a week is music to Allegri’s ears. They have conceded the fewest shots this season, with keeper Mike Maignan only facing 16 in four games.

There is a cohesion to the defence already that was missing throughout 2024-25. Of course, this was always going to be the case with Allegri. Defensive solidity comes first and foremost, but he has also made Milan into a strong attacking unit, with wily old sage Luka Modric at the heart of everything in midfield, arguably the first time they have had a midfielder of that ilk since Pirlo left 14 years ago.

On paper, Milan are not good enough for a title tilt, yet everyone said the same of Conte’s Napoli a year ago. A win in San Siro would send a signal that Max is indeed back, and Milan are to be taken seriously.

The midfield battle between Modric and De Bruyne could prove to be a tasty affair, but all eyes will be on Conte and Allegri. The two superstar coaches whose fate has never truly intertwined yet still influenced the other.

Conte has five wins from eight against Allegri, will Sunday be the sixth?