AC Milan host Napoli in this weekend's headline Serie A clash, as both teams look to stamp their authority on this season's title race. Sunday's keenly anticipated fixture pits Massimiliano Allegri against Antonio Conte, two men who previously enjoyed a close affiliation with Juventus.
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The fifth matchday of the new Serie A campaign bears witness to the biggest fixture of the season so far, as Napoli travel north to face AC Milan at the San Siro. The outcome could have a major bearing on the title race, even at this early stage of the campaign.
Antonio Conte's Napoli currently sit at the summit of the Serie A table after winning each of their opening four fixtures, and consequently sit three points ahead of third-placed AC Milan. Although their league form has been faultless, the Azzurri did suffer a disappointing loss to Manchester City in the opening week of Champions League action. Meanwhile, Milan have amassed nine points following victories over Lecce, Bologna, and Udinese, and have breezed through to the third round of the Coppa Italia.
Will Napoli have extended their lead at the top come Monday morning, or can Milan exploit their home advantage with the help of a boisterous San Siro crowd?
As this promises to be a close encounter, it's difficult to predict exactly what will happen. However, by analysing the stats and reviewing the form guide, we've been able to provide you with a handful of data-driven betting tips for Sunday's high-profile contest.
AC Milan v Napoli tips: Sunday, September 28th, 19:45 (BST)
Double Chance - Napoli or Draw: 4/7 (bet365)
Christian Pulisic to score or assist: 13/10 (bet365)
Odds courtesy of bet365. Correct at the time of publication and subject to change.
Napoli likely to claim a positive result at the San Siro
Napoli's recent record speaks for itself; the Azzurri have avoided defeat in ten of their last twelve visits to the San Siro when facing AC Milan. Under the stewardship of Antonio Conte, the Naples-based outfit have lost just twice in their last 21 away fixtures in the league, helping them to emerge as the Serie A's strongest side.
However, write off AC Milan at your peril. The Rossoneri overcame Napoli on home soil as recently as February 2024, when Frenchman Theo Hernández netted the evening's only goal. This will undoubtedly give them confidence heading into Sunday's tie, which will also be staged in the Lombardy capital.
There have been three draws in the last six meetings between these opponents, so don't be surprised if this one ends all-square. Napoli are arguably even better equipped than they have been in the last two seasons, but these two Italian giants are still fairly evenly matched.
For the reasons outlined above, pursuing the Napoli/Draw double chance bet feels like an astute course of action.
Tip: Double Chance - Napoli or Draw: 4/7 (bet365)
Explanation: This bet lands if either Napoli win or the match ends in a draw.
Pulisic - Milan's star man
Following his arrival in Italy in the summer of 2023, Christian Pulisic has established himself as one of the Serie A's best attacking players. The American international has registered 26 goals and 18 assists in his 74 Italian top-flight appearances, matching the direct goal contribution record of Inter Milan talisman Lautaro Martínez within this period.
Pulisic has made a scintillating start to the 2025/26 campaign, claiming five goals and one assist across all competitions. Consequently, he's averaged 1.41 goals and 0.47 assists every 90 minutes, putting him firmly in the top percentile of Serie A competitors.
If he can replicate his recent form on Sunday, it's likely Christian Pulisic will make yet another decisive impact in the attacking third.
Tip: Christian Pulisic to score or assist: 13/10 (bet365)
Explanation: This bet will land if Christian Pulisic registers a goal or an assist at any stage during the match.
Defensive discipline on show
Milan preside over an extremely strong defensive record. Allegri's men have kept three clean sheets in their opening four Serie A outings, conceding just two goals in the process - a marked improvement on last season's general performance.
Meanwhile, Napoli have prevented the opposition from scoring in 11 of their last 21 away fixtures, a record that few other teams in world football, never mind the Italian top-flight, can boast.
Nevertheless, the Azzurri have sometimes lacked an attacking edge when playing away from the Diego Maradona Stadium. This, coupled with their impressive defensive performances on the road, has resulted in seven of Napoli's last eight away matches producing two goals or fewer.
As a result, we should expect a tense and cagey affair at the San Siro, with potentially few clear-cut goalscoring opportunities.
Tip: Under 2.5 Goals: 4/6 (bet365)
Explanation: This bet lands if fewer than three goals are scored during the match.
AC Milan v Napoli - Match Result market
Odds correct at time of publication and subject to change.
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Odds correct at time of publication and subject to change.