The 2025 Italian Super Cup kicks off on Thursday with two intriguing semi-final clashes, leading to a final at King Saud University Stadium in Riyadh, Saudi Arabia. The winners of Thursday and Friday’s matches will meet for the coveted trophy.

Napoli vs. AC Milan: A First-Ever Super Cup Meeting

The opening semi-final features last season’s Serie A champions, Napoli, taking on AC Milan, who finished just a point above them in the league. Interestingly, this will be the first time the two sides meet in the Supercoppa Italiana.

Milan have the potential bonus of facing city rivals Inter in the final, should both clubs overcome their semi-final opponents. Inter face Bologna on Friday.

Milan lifted the trophy last season, while Inter claimed the three titles before that. Across the 37 editions of the competition, the two Milan clubs have dominated, winning 16 titles between them (eight each).

Napoli, meanwhile, are chasing their first Super Cup triumph since the 2014/15 season under Rafael Benitez, with only one prior win in 1990/91 under Alberto Bigon.

Bologna Eyeing a Historic Win

Vincenzo Italiano’s Bologna will aim for their first-ever Supercoppa Italiana victory if they can get past an Inter side currently leading the league.

Stats Suggest a Tight Contest

The form of all four sides hints at closely contested semi-finals. Bologna may be six points behind the other three teams, but they have lost the same number of league games as Napoli and Inter (four each).

Milan have only suffered one defeat—a 1-0 loss to Cremonese—but have drawn five games, more than any of the other teams, and won nine matches, fewer than Inter (11) and Napoli (10), and only two more than Bologna (7).

Defensively, Inter have conceded 14 goals, while Milan, Bologna, and Napoli have all conceded 13. Offensively, Inter lead with 34 goals, while Milan, Bologna, and Napoli are close behind with 24, 23, and 22, respectively.

Napoli’s Recent Woes

Napoli enter the clash under pressure, having lost 2-1 at Benfica in the Champions League, leaving them precariously close to the playoff zone. They followed that defeat with a 1-0 loss to Udinese, courtesy of Jurgen Ekkelenkamp’s late strike.

Milan’s Star to Watch: Pulisic

Christian Pulisic has been instrumental for Milan this season, scoring seven league goals—just one behind Inter’s Lautaro Martinez, despite playing five fewer games. He scored the winner in Milan’s 2-1 victory over Napoli and will be key again. Milan recently dropped points in a 2-2 draw with Sassuolo, allowing Inter to reclaim the top spot.

Napoli’s Away Struggles

Head-to-head records are tight: both Milan and Napoli have won seven of their last 20 encounters, with six draws. Napoli’s main challenge has been their away form, losing seven games outside Naples this season. Despite a neutral venue in Riyadh, this trend could be crucial. Romelu Lukaku may return to the squad after overcoming injury, offering Conte a boost.

Milan Chasing Ninth Title

Max Allegri’s Milan remain unbeaten away from San Siro. A victory in Riyadh would give them a ninth Super Cup title, drawing level with Allegri’s former club, Juventus. Luka Modric’s creativity will be key in unlocking defenses, while Allegri must decide whether to pair Pulisic with Rafa Leao or Christopher Nkunku.

Inter vs. Bologna: Injury Concerns for Nerazzurri

Inter have been strong defensively, conceding only three goals in their last five games across competitions. Bologna, however, may benefit from several Inter injuries, including key players Hakan Calhanoglu, Francesco Acerbi, Matteo Darmian, Denzel Dumfries, Thiago Tomas Palacios, and backup goalkeeper Raffaele Di Gennaro.

Surprisingly, Bologna have had the edge in recent Serie A head-to-heads with Inter: two 2-2 draws, one Inter win (1-0), and two Bologna victories (1-0 each).

With Milan, Napoli, Inter, and Bologna all closely matched, the upcoming Italian Super Cup promises to deliver drama, high-quality football, and possibly historic moments in Riyadh.