19:30 BST, Saturday 25 August - Stadio San Paolo (Naples)
Maurizio Sarri set a high bar at Napoli last term, leading the club to a second-place finish with their highest ever points tally.
It would never be an easy act to follow but Carlo Ancelotti wasn’t about to shirk the challenge. This is the man who didn't think twice about stepping into the shoes of Pep Guardiola or Jose Mourinho.
Having guided the club to victory in his first game in charge, he will now look to back that up with a win on home soil against a top four rival.
The Morandi bridge tragedy in Genoa forced the cancellation of Milan’s opener so this game will offer a first glimpse of the new-look squad as they begin their quest to break into the top four.
Last Time Out
Lazio 1-2 Napoli (Serie A)
Napoli’s opener began badly as Lazio outplayed them in the opening 25 minutes in Rome. They fell behind to a fine curled effort from Ciro Immobile before working their way back into the game.
Arkadiusz Milik had a goal ruled out by VAR due to a foul in the build-up but struck again just before half-time to level the scores, tapping in a Callejon knock-down from close range.
A strong second half performance rewarded Ancelotti's men with a goal on the hour mark, Insigne guiding the ball home from eight yards.
A late surge from the home side spawned a chance for Francesco Acerbi, who slammed his shot into the post.
Real Madrid 3-1 Milan (Friendly)
There has been much anticipation about what this Milan side can achieve. Their last action came in a pre-season friendly defeat to Real Madrid.
They started poorly conceding after just two minutes but responded quickly through new signing Gonzalo Higuain.
The Spaniards edged in front through Gareth Bale in the dying seconds of the first half before Mayoral added another just before the final whistle after a flurry of second-half substitutions.
Despite the result, it was a solid performance to follow up to the 1-0 win over Barcelona for Gennaro Gattuso’s men.
Carlo Ancelotti is expected to show faith in the XI that passed the first test against Lazio last weekend.
Amin Younes, Faouzi Ghoulam and Alex Meret are all out injured for the Partenopei.
A heart condition has ruled out left back Ivan Strinic while fellow fullback Andrea Conti is still recovering from a knee operation.
Hakan Calhanoglu is suspended so new signing Diego Laxalt could slot in on the left of midfield with Bonaventura pushed further forward instead of Fabio Borini.
Gattuso used Patrick Cutrone on the left of a front three for a spell against Real Madrid but the youngster is likely to start on the bench.
Key Battle: Carlo Ancelotti (Napoli) vs Gennaro Gattuso (Milan)
The battle between the master and former pupil will intrigue many.
Ancelotti has taken charge of a team drilled to precision by his predecessor. His task will be to oversee a transition of styles while maintaining a title challenge.
Gattuso spent eight years playing under the Napoli boss during which Milan lifted eight trophies. He will hope to emulate some of that success during his tenure at the Giuseppe Meazza.
The Rossoneri have strengthened this summer, on and off the field. There is a consensus they now have all the tools available to make a top four challenge.
Gattuso must prove he is the right man for the job rather than another faulty cog in the machine.
Is Aurelio De Laurentiis fully focused on Napoli?
As Ancelotti prepared his team for this game, club Chairman Aurelio De Laurentiis was giving a press conference in Bari to present plans for reviving the bankrupt club from Puglia.
The former film producer announced his son Luigi as new president and Matteo Scala as the coach. He stated their aim was to return to Serie A as quickly as possible. Bari will begin their quest in the fourth tier of Italian football in the coming weeks.
However, there are fears among Napoli fans the enigmatic owner could lose interest in the Azzurri as he strives to replicate their revival at a rival club.
Banners appeared across the city following the announcement: some asking for respect, others directly threatening or insulting the owner over his actions.
Prediction: Napoli 2-1 Milan
Napoli are unbeaten in seven matches against Milan of which they won five including the last two at the San Paolo.
Ancelotti’s men already have a win under their belts while this will be the Rossoneri’s first taste of competitive action this campaign.
Expect a close game, but the home side should come away with all three points.