Napoli and Milan Braced for Italian Super Cup Showdown, Penalty Blues in Tow

Stage Set for the Italian Super Cup

Tonight, the Italian Super Cup kicks off with a high-stakes duel between Napoli and Milan at Al-Awwal Park in Riyadh, broadcast exclusively on the Eight app, the Saudi Pro League’s official partner.

Two Semis, One Final Destination

The other semi-final, Inter versus Bologna, takes place tomorrow evening to decide the second finalist for the final showdown.

As per the competition rules, the winner is decided in 90 minutes, or directly by penalties with no extra time.

A look at penalty history reveals that Napoli and Milan carry different fortunes on the shoots, with memory of past misses and decisive kicks shaping expectations for tonight’s clash.

Napoli’s Rasmus Hojlund has taken three penalties in his career and missed only the one when wearing Napoli’s colours against Qarabağ in a Champions League tie, while Scotland’s Scott McTominay converted his only penalty for his country against Greece in March 2025.

Noa Lang has converted seven of nine career penalties, and David Neres has missed a Napoli-kick in an Italian Cup meeting against Cagliari, underscoring the nerves factor ahead of a shootout if it comes to that.

For Napoli, Matteo Politano boasts 10 goals from 14 penalties; Luka Modrić has 24 successes from 30 attempts; Christopher Nkunku has converted 3 of 15; Adrien Rabiot and Alexis Saelemaekers have yet to be tested in a high-stakes shootout at this level; Rafael Leão has two goals this season and four of five in his career, but missed a Portugal penalty against Luxembourg in 2023.

In Milan’s corner, Christian Pulisic remains their most reliable taker, though he has two misses in 15 attempts, both with the club.

Overall, the two teams arrive with a history of penalty drama, and tonight’s outcome could hinge on who handles the pressure when the shootout lights go on, or simply on who scores first from the spot.

And if the match ends in a stalemate after 90 minutes, fans will be treated to the spectacle of a high-stakes shootout—no extra time, just pure nerves and precision.

Humor break: If penalties were a sniper test, Napoli and Milan would both miss, then blame the wind, the goalposts, and the referee’s shoelaces—classic crosshair comedy with a football twist.