The first of the two semis sees last season's Serie A winners, Napoli, take on AC Milan, who are just a point and a place above them in the Italian top-flight.
Milan could meet Inter in the final
It will actually be a first-ever meeting between the two teams in the competition, with Milan having the bonus of meeting city rivals, Internazionale, in the final, should the Rossoneri and Nerazzurri overcome their opponents (Inter meet Bologna on Friday).
Milan won the trophy last season, of course, with Inter taking the three previous titles. Of the 37 occasions the competition has taken place to date, 16 of them have been won by either Milan club (eight each).
The Partenopei haven't triumphed in the competition since the 2014/15 season under Rafael Benitez, and Napoli's only previous win before that came way back in 1990/91 under Alberto Bigon.
Vincenzo Italiano's Bologna side will be looking for their first-ever Supercoppa Italiana victory if they can make it past an Inter side that are the team to beat in the league this season.
Stats show how equal all four teams are
The current form of all four sides is likely to be an accurate guide as to what to expect in the semis, and though Bologna are at least six points behind the other three teams, they have only lost the same number of league games as Napoli and Inter (four).
Milan has only lost once - a 1-0 defeat to Cremonese, but has drawn the most of all four teams (five), and won fewer games (nine) than Inter (11) and Napoli (10), and only two more than Bologna's seven.
In terms of goals against, Inter have let in 14, with the other three teams all having conceded 13, and on goals scored, the Nerazzurri are way out in front with 34.
Only Sassuolo's 21 goals come close to the amount that Milan (24), Bologna (23) and Napoli (22) have scored since the start of the 2025/26 Italian top-flight campaign.
Napoli's recent wobble
For Antonio Conte, Napoli's form immediately preceding this Thursday's game may be of concern.
A Champions League defeat at Benfica kept them just about in the top 24 teams, the top eight of whom automatically qualify for the knockout rounds, and the other 16 of which have to do battle in the playoffs.
Only Copenhagen, in 24th position, remain below them in the playoff positions, whilst the Portuguese giants, Pafos and Union Saint-Gilloise, are just a point behind them in the standings.
On the back of that loss at the Estadio da Luz, the Partnopei were then defeated by Udinese, thanks to Jurgen Ekkelenkamp's 73rd-minute winner.
Pulisic the man to watch for Milan
Milan's run of form includes beating Inter and Napoli, the latter match decided by Christian Pulisic in a 2-1 victory, despite having Pervin Estupinian sent off.
Pulisic is certainly one to watch again here, as the American is enjoying a vintage season heading into a World Cup being played in his backyard.
At present, the 27-year-old's seven league goals see him just one behind Inter's Lautaro Martinez at the top of the Serie A scoring charts. However, it's worth pointing out that he's played five fewer games than the Argentinian in 25/26.
Milan also dropped points at the weekend, drawing 2-2 with Sassuolo, which allowed Inter to leapfrog them into top spot.
Napoli's away form a worry for Conte
The head-to-head record between Milan and Napoli has seen both win seven of the last 20 meetings, with six being drawn, though the Partenopei's away form appears to be what's hampering Conte.
In all competitions, they've lost seven outside of Naples, and yet have remained unbeaten at Stadio Diego Armando Maradona in 2025.
Their four Serie A defeats in 25/26 have also all occurred away from home. Though Saudi Arabia provides a completely neutral venue, it will be interesting to see if their travails continue.
One positive note is that striker Romelu Lukaku could be named in the squad for the first time in months after recently overcoming his injury.
Milan could draw level with Juve on nine titles
Max Allegri's Milan side are unbeaten away from San Siro, and were they to emerge victorious in this competition, a ninth title would bring them level with Allegri's former employers, Juventus.
Luka Modric is enjoying a renaissance in Milan and should provide the creativity that allows Pulisic to do his best work.
Santiago Gimenez is unlikely to play a part, so one of Allegri's main decisions is whether he partners the American with Rafa Leao or Christopher Nkunku.
With four wins from their last five in all competitions and only three goals conceded in that time, Cristian Chivu's Inter side are likely to be a tough nut to crack for a Bologna squad that didn't win any of their last three Italian top-flight games.
Inter would appear to have several injuries, however, and some to key players, handing Bologna a potential advantage.
Francesco Acerbi, Hakan Calhanoglu, Matteo Darmian and Denzel Dumfries are all out, along with Thiago Tomas Palacios and second-choice goalkeeper, Raffaele Di Gennaro.
In the last five Serie A head-to-heads, perhaps surprisingly, Bologna hold the edge.
Two games have been drawn 2-2, Inter have won one 1-0, whilst La Rossa have won two, also by a goal to nil on each occasion.
A fascinating few games are therefore in prospect.
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