The two giants of Calcio take a brief break from Serie A duty to face each other in the 234th Derby della Madonnina - with the Nerazzurri having won 85 and their Rossoneri rivals 79 - yet this marks only the second Supercoppa meeting between them.
Match preview
The only previous Milan derby in Italy's super-cup competition came back in August 2011, when the Rossoneri won 2-1 under then-manager Max Allegri, with goals from Zlatan Ibrahimovic and Kevin-Prince Boateng following Wesley Sneijder's strike for Inter.
Now, following their league victory at the start of September, Milan could now win consecutive games against their fiercest foes for the first time since that very same year.
A Rafael Leao brace proved crucial in their 3-2 success at San Siro, but the Scudetto-holders - who dethroned Inter by pipping them to the post in a dramatic title race last year - must now repeat the trick in the very different surrounds of Saudi Arabia, where King Fahd Stadium will host the clubs' latest contest.
Stefano Pioli's side have stumbled their way into the Supercoppa, though, after frittering away two points at home to Roma by blowing a two-goal lead, then exiting the Coppa Italia to Torino, before salvaging a 2-2 draw in Lecce last weekend.
The latest team to find themselves fully tested at Stadio Via del Mare, Milan were two down after 23 minutes to last term's Serie B champions, but Leao and captain Davide Calabria struck back after the break to limit the damage and save some face.
Nonetheless, the Rossoneri sit some nine points adrift of Serie A leaders Napoli following the Partenopei's 5-1 destruction of Juventus on Friday, so have plenty of ground to make up in the second half of the season if they are to retain their crown.
Claiming some silverware at the expense of their city rivals would certainly prove a good way to kickstart 2023 for Pioli and co, and in 34 previous editions of the Supercoppa, 71% have been won by the league champions.
Set to contest only the third final between the two Milanese heavyweights - after the Coppa Italia of 1977 and the Supercoppa 12 years ago - Inter are seeking their first such victory.
Having beaten Juventus to the Coppa last spring, via a 4-2 extra-time victory in Rome, the Nerazzurri will now be aiming to win successive super-cups for the first time since 2006 - with Juve also their victims in last January's showpiece at San Siro.
Inter warmed up for the task with a victory over Verona on Saturday, in which Lautaro Martinez found the bottom corner in the third minute and Simone Inzaghi's side simply strangled the life out of the remainder of the game.
After seeing off the Serie A strugglers, they have won eight of their last 10 in the top flight - including against previously unbeaten Napoli - and they join Juventus in third place; within a point of Milan.
Last week's Coppa Italia clash with Parma almost ended in embarrassment for Inzaghi, but his team squeezed through to the quarter-finals by finally beating the Serie B outfit, who led until the 88th minute, when Martinez equalised, and Francesco Acerbi's header edged them through in extra time.
That continues a run of good fortune in the cups for Inter's much-maligned coach, who has not only guided them through to the Champions League knockout stages again this year but has also won each of his three Supercoppa contests as a manager: two with Lazio and one for his current employers.
Entering elite company, he would equal coaching legends Marcello Lippi and Fabio Capello (both four) with the most wins in the competition should the Nerazzurri prevail on Wednesday.
AC Milan form (all competitions):
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Inter Milan form (all competitions):
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Team News
After his side struggled without influential midfielder Sandro Tonali on Saturday, as the Italy international served a one-match Serie A suspension, Stefano Pioli will be glad to welcome him back in midweek.
Divock Origi and veteran defender Simon Kjaer both returned from injury at the weekend, and the latter could be in contention to start. However, ex-Inter striker Zlatan Ibrahimovic joins Rade Krunic, Ante Rebic and first-choice goalkeeper Mike Maignan on the sidelines once again.
Despite a hectic schedule, Olivier Giroud continues to lead the line up front, while Brahim Diaz can see off competition from Charles De Ketelaere to fill the trequartista role in Pioli's trademark 4-2-3-1 formation. Giroud will bid with fellow 36-year-old Edin Dzeko to become the oldest player to find the net in Supercoppa history; overtaking Cristiano Ronaldo (35 years and 350 days, for Juventus versus Napoli in 2021).
After nine appearances without netting against Inter, leading scorer Rafael Leao bagged a brace in September's derby, and the Portuguese winger will feature on the Rossoneri's left flank.
Meanwhile, Inter striker Romelu Lukaku took part in group training at the start of the week, with the aim of being passed fit to play a part on Wednesday evening.
However, both club captain Samir Handanovic and midfielder Marcelo Brozovic have been ruled out by Simone Inzaghi due to their injury problems.
In Lukaku's absence from the first XI, Dzeko should partner Lautaro Martinez in attack. After scoring against Juventus in last January, 'El Toro' could become the first player to score in successive Supercoppas since compatriot Carlos Tevez, who did so in 2013 and 2014.
AC Milan possible starting lineup:
Tatarusanu; Calabria, Tomori, Kalulu, Hernandez; Bennacer, Tonali; Saelemaekers, Diaz, Leao; Giroud
Inter Milan possible starting lineup:
Onana; Skriniar, Acerbi, Bastoni; Dumfries, Gagliardini, Calhanoglu, Mkhitaryan, Dimarco; Martinez, Dzeko