Previous winners of the competition, Napoli and AC Milan, will compete in the first semi-final of the 2026 Supercoppa Italiana on Thursday.
Serie A champions Napoli will take on the challenge of beating the winners of last year’s tournament at the King Saud University Stadium. Riyadh will be the neutral home ground for the mouth-watering encounter between two of the biggest heavyweights in Italian football.
Previous winners will compete against each other in Riyadh
Napoli and AC Milan have won the Supercoppa Italiana ten times since 1988, with the latter lifting the trophy an impressive eight times.
Domestically, both sides are flying high, with AC Milan only recently losing their place at the top of the Serie A standings to arch-city rivals Inter last weekend. However, Napoli are third, only one point behind. Remarkably, only three points separate the top four teams. Where AS Roma forms the leading quartet of teams.
Looking back at last year’s final, it was an unmissable encounter between AC Milan and Inter Milan, with Tammy Abraham scoring the match-winner deep into second-half stoppage time. The 3-2 victory stunned everyone present at the King Saud University Stadium on January 6.
The winner could equal Juventus’ record of lifting the Supercoppa Italiana trophy nine times.
Could recent form on Thursday evening be the deciding factor?
Napoli has suffered a mini dip in form in recent weeks, after consecutive defeats in all competitions.
The jubilation over the 2-1 victory over Juventus on December 7 was quickly forgotten when Antonio Conte’s side were defeated 2-1 by Benfica in the Champions League three days later.
That defeat was followed by an unforeseen 1-0 loss to Udinese in Serie A, when Jurgen Ekkelenkamp’s 73rd minute match-winner condemned Napoli to their fourth league defeat of the season.
On the other hand, AC Milan are unbeaten in 14 league matches dating back to the closing stages of August, led by Massimiliano Allegri.
While Thursday evening will focus on the Supercoppa Italiana, Allegri’s AC Milan tactics have put San Siro Stadium residents on notice of a potential domestic double, in addition to a 20th Scudetto shield.
Despite being the first head-to-head meeting in the Supercoppa Italiana, AC Milan have only lost two of their previous eight matches of that particular nature. However, Napoli were victorious in two of the previous three games of that nature, but goals from Alexis Saelemaekers and Christian Pulisic helped Allegri’s men to a 2-1 win in September.
Could Napoli’s plethora of injuries be their downfall?
While AC Milan cannot rely on the long-term injuries of Rafael Leão, Santiago Giménez and Youssouf Fofana, Napoli will be seriously exhausted on Thursday, to say the least.
Frank Anguissa, Juan Jesus, Kevin De Bruyne, Billy Gilmour and Romelu Lukaku will all miss the match, indicating Napoli could struggle in front of goal. De Bruyne’s talisman has scored four league goals this season, while Lukaku has not played a minute of football in the 2025/2026 season due to a persistent thigh injury.
Together with his national and international compatriot Scott McTominay, Gilmour will suffer a big loss in the middle of the field. Another big defensive loss is Anguissa, whose bread and butter is sitting in front of the back four and being their first line of defense in attack.
The loss of big players, including De Bruyne, Lukaku and Anguissa, could give AC Milan the advantage on paper. But as everyone knows, anything can happen on the field in what all football fans call the beautiful game.
The winners will face Inter Milan or Bologna in the final, who will play each other on Friday. Can we expect a repeat of last year’s unforgettable spectacle, and a 243rd competitive Derby della Madonnina, if AC Milan and Inter can both reach the final hurdle again?
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