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Previous winners of the competition, Napoli and AC Milan, lock horns in the first semi-final of the 2026 Supercoppa Italiana on Thursday.
Serie A champions Napoli will tackle the challenge of beating the winners of last year’s tournament at the King Saud University Stadium. Riyadh will be the neutral home for the mouth-watering encounter between two of the biggest heavyweights in the Italian football ring.
Previous winners will go head-to-head in Riyadh
Napoli and AC Milan have won the Supercoppa Italiana 10 times since 1988, with the latter lifting the trophy on no less than eight occasions.
Domestically, both sides are flying high, with AC Milan only recently losing their perch at the top of the Serie A standings to arch city rivals Inter this past weekend. However, Napoli are in third, trailing by only a point. Remarkably, only three points separate the top four sides. With AS Roma making up the distinguished quartet of teams.
Looking back at last year’s final, it was an unmissable encounter between AC Milan and Inter Milan, where Tammy Abraham netted the match-winner deep into second-half stoppage time. The 3-2 win amazed everyone in attendance at the King Saud University Stadium on 6th January.
The winner could equal Juventus’ record of lifting the Supercoppa Italiana trophy on a currently unparalleled nine occasions.
Could recent form be Thursday night’s deciding factor?
Napoli have been in a mini-slump of form in recent weeks, after consecutive defeats across all competitions.
The jubilation of beating Juventus 2-1 on December 7th was quickly forgotten as Antonio Conte’s side were beaten 2-1 by Benfica in the Champions League three days later.
That defeat was followed by an unforeseen 1-0 loss to Udinese back in Serie A as Jurgen Ekkelenkamp’s 73rd-minute match-winner condemned Napoli to their fourth league defeat of the season.
On the other boot, AC Milan are unbeaten in 14 league matches, dating back to the concluding stages of August, under the expert stewardship of Massimiliano Allegri.
While Thursday night will concentrate on the Supercoppa Italiana, Allegri’s AC Milan Tactics have put the San Siro Stadium natives on notice of a potential domestic double, alongside a 20th Scudetto shield.
Despite it being the maiden head-to-head encounter in the Supercoppa Italiana, AC Milan have lost only two of the previous eight matches of that particular nature. However, Napoli have triumphed in two of the previous three games of that nature, but goals from Alexis Saelemaekers and Christian Pulisic helped Allegri’s men in a 2-1 win in September.
Could Napoli’s abundance of injuries be their downfall?
While AC Milan cannot call upon long-term injury victims Rafael Leão, Santiago Giménez and Youssouf Fofana, Napoli will be severely depleted on Thursday to say the very least.
Frank Anguissa, Juan Jesus, Kevin De Bruyne, Billy Gilmour and Romelu Lukaku will all miss the game, which indicates that Napoli could struggle in front of goal. The talismanic De Bruyne has scored four league goals this season, while Lukaku hasn’t played a single minute of football in 2025/26, due to an ongoing thigh injury.
Alongside his domestic and international compatriot Scott McTominay, Gilmour will be a huge loss in the middle of the pitch. Another huge defensive loss is Anguissa, whose bread and butter is to sit in front of the back four and be their first line of defence upon attack.
The loss of big hitters, including De Bruyne, Lukaku and Anguissa, could give AC Milan the advantage on paper. However, as everyone knows, anything can happen on the pitch across what all football supporters refer to as the beautiful game.
The winners will face either Inter Milan or Bologna in the final, who clash on Friday. Could we be in for 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?
