| Moneyline Pick | AC Milan to win (+165) |
| Player Prop | Christian Pulišić(+250) |
| Same Game Parlay | AC Milan to win + Pulišić to score + under 2.5 goals (+TBC) |
| Check Live Odds | |
Napoli vs AC Milan Main Match Info
- Date and Kickoff Time: Thursday, December 18, 2025, 2:00 PM ET
- Stadium: Al-Awwal Park
- Location: Riyadh, Saudi Arabia
- Tournament: Italian Super Cup (Supercoppa Italiana) Semi-Final
- Last H2H match: AC Milan 2-1 Napoli (Serie A 2025-2026 season, September 2025)
Napoli vs AC Milan Prediction
- Moneyline Pick: AC Milan to win
- Odds: +165 (Tonybet)
Despite Napoli leading the historical head-to-head record with fourteen victories to Milan’s ten, we favor AC Milan to win this Super Cup semi-final.
Since joining AC Milan in May 2025, Massimiliano Allegri has successfully implemented a solid defensive system that has propelled Milan to second place in Serie A.
With Napoli having lost their last two matches across all competitions and lacking home advantage in neutral Riyadh, Milan’s defensive discipline should prove decisive.
This was evident in their September 2025 Serie A meeting, where Massimiliano Allegri’s defensive organization secured a 2-1 victory for Milan.
Napoli vs AC Milan Player Prop
- Prop Bet: Christian Pulišić to score
- Odds: +280 (Tonybet)
Pulišić has become one of Massimiliano Allegri’s most trusted attacking players since the coach joined Milan, featuring prominently in the team’s setup even when tactical adjustments are needed, as seen in the recent Sassuolo match.
The American forward scored a brace against Torino and leads Milan with seven goals across all competitions this season.
Napoli vs AC Milan Same Game Parlay
- SGP: AC Milan to win + Christian Pulišić to score + under 2.5 goals
- Odds: TBC (Tonybet)
With Antonio Conte and Massimiliano Allegri, two of Italy’s most defensively-minded coaches, on the touchline, this semi-final is likely to be a low-scoring tactical battle.
Allegri prefers a controlled tactical approach with compact defensive shape, capitalizing on opponent errors rather than taking unnecessary risks.
Napoli vs AC Milan Team News
Napoli Team News
Until recently, Napoli led the three-way Serie A title race, but a 1-0 defeat to Udinese last weekend dropped Antonio Conte’s side from first to third place.
Despite dominating possession, Napoli struggled to control the game. They lacked penetration against Udinese’s defensive block, managing only 8 shots compared to their opponents’ 19. Napoli finished the match with under 1.0 expected goals (xG), while Udinese secured victory with a second-half goal.
⏹️ Full time: #NapoliJuventus 2-1 💙💙💙💙💙
💙 #ForzaNapoliSempre pic.twitter.com/rboIhwgZOY
— Official SSC Napoli (@sscnapoli) December 7, 2025
Napoli’s struggles have extended to the Champions League, where they produced an underwhelming performance in a 2-0 defeat to Benfica, again dominating possession but failing to create clear chances.
As a result, Napoli sit 23rd in the Champions League standings and must defeat Copenhagen in their final group match to secure knockout stage qualification.
Alex Meret, André-Frank Zambo Anguissa, Billy Gilmour, and Kevin de Bruyne are sidelined due to injuries. Romelu Lukaku and Juan Jesús are awaiting medical clearance.
AC Milan Team News
Under Massimiliano Allegri, Milan (currently 2nd in Serie A) are known for tight, defensively sound performances, though recent results haven’t always followed that script. Defensive lapses were evident in last weekend’s 2-2 draw with Sassuolo, where Milan surrendered a lead.
Recent weeks have been challenging for Massimiliano Allegri, with multiple forward injuries impacting the team’s attacking options immediately.
Milan first fell to a late Lazio goal in what had been a closely-contested match.
Massimiliano Allegri with the Philadelphia Coach of the Month award for November 🏆👏 pic.twitter.com/loWHf01ro7
— Lega Serie A (@SerieA_EN) December 14, 2025
This was followed by a chaotic 3-2 victory over Torino, where Pulisic (‘Captain America’) proved decisive with a brace. Despite dominating the match, Milan only found their rhythm and secured the win in the second half.
Against Sassuolo, Milan struggled with midfield control and couldn’t contain Armand Laurienté in the second half. Allegri’s tactical adjustments, including withdrawing a forward to shore up midfield, ultimately secured only a point.
Rafael Leão, Santiago Giménez, Matteo Gabbia, and Youssouf Fofana will be sidelined due to injuries.
Napoli vs AC Milan: Where to Watch (Canada)
- DAZN Canada
- TLN
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