The sides have won 113 major honours between them down the years, but reigning Serie A champions Juve have the edge ahead of this latest tussle at the King Abdullah Sports City Stadium.
Whereas Milan's last piece of silverware came in this showpiece fixture three years ago, Juventus have won trophy after trophy under Massimiliano Allegri.
The Bianconeri have won four successive Serie A and Coppa Italia doubles, most recently finishing four points clear of Napoli to lift their 34th top-flight crown, while also seeing off Milan 4-0 in the domestic cup final.
That comfortable victory at the Stadio Olimpico in Rome last May, with all four goals coming in a 20-minute burst in the second half, cemented Juve's status as the undisputed kings of Italian football.
The bad news for Juventus's rivals is that they have only got stronger by adding Cristiano Ronaldo to their already talented squad for this season, and it has told as the Old Lady have dropped just four points from a possible 57.
It could well turn out to be a record-breaking season for Allegri's men, who also remain on course to make it five in a row in the Coppa Italia, having overcome Bologna on Saturday to set up a quarter-final tie with Cagliari or Atalanta.
Juve have lost just two of their 26 matches in 2018-19, both coming in the Champions League group stage - though not enough to prevent them from reaching the knockout rounds of the competition with relative ease - and only four teams have stopped them from winning overall.
After returning from their two-week winter break with a convincing win over Bologna in the cup, sealing their victory through goals early in either half from Federico Bernardeschi and Moise Kean, Juve now have 2019's first piece of silverware firmly in their sights.
Recent form (all competitions): LWWDWW
Milan may be Juve's closest rivals in terms of major honours accrued, but there is a chasm between the two heavyweight clubs ahead of this showdown in the Middle East.
The Rossoneri have not won a league title since 2011 and, incredibly, they last went all the way in the Coppa Italia 16 years ago when beating Roma 6-3 on aggregate in the final.
Winning silverware this season also looks a difficult prospect as Milan, now under the management of iconic player Gennaro Gattuso, face Napoli in the last eight of the Coppa and are 22 points adrift of Serie A pacesetters Juventus.
Finishing fourth appears to be the target for Gattuso over the remaining four months of the campaign, meaning a return to the Champions League following a five-season absence.
Milan stuttered ahead of the winter break, going four matches without a win prior to their 2-1 victory over SPAL on December 29, though even then they looked unconvincing as they recovered from a goal down on home soil.
Gattuso's men failed to score a single goal during that four-match winless run, playing out stalemates with Torino, Bologna and Frosinone, while also losing 1-0 to Fiorentina.
Serious questions were asked of the manager's future at that point, though the board publicly backed Gattuso and former defensive midfielder now has a chance to put things right.
Recent form (all competitions): LDLDWW
Juventus have a number of injury concerns for Wednesday's match, but even so Allegri will still be able to choose from three of his four regular defenders.
Mario Mandzukic will play no part in Jeddah, however, which will force Allegri into a reshuffle up top and will likely mean Ronaldo leading the line.
A good showing from Douglas Costa at the weekend should cement his place in one of the wide attacking positions, with Paulo Dybala favourite to start on the opposite side and Bernardeschi providing support from the bench.
Gonzalo Higuain is eligible to play for Milan against the club he is still contracted to, meanwhile, and he is expected to start here despite doubts over his future at San Siro.
Gattuso will have to contend without suspended forward Suso, who has played a direct part in 12 goals in 18 Serie A starts this term, so Lucas Paqueta could make his second appearance for the club since joining from Flamengo.
Juventus possible starting lineup:
Szczesny; De Sciglio, Bonucci, Chiellini, Sandro; Bentancur, Pjanic, Matuidi; Dybala, Ronaldo, Costa
AC Milan possible starting lineup:
Donnarumma; Calabria, Zapata, Romagnoli, Rodriguez; Calhanoglu, Kessie, Bakayoko, Paqueta; Higuain, Cutrone
Head To Head
Juventus have won each of their last six meetings with Milan in all competitions since losing on penalties in the 2016 Supercoppa Italiana clash in Qatar.
Going further back, it is just two wins in 17 meetings for the Rossoneri in this fixture, the other coming in a Serie A clash at San Siro in October 2016.
The most recent meeting in November ended in a 2-0 triumph for Juve, as Mandzukic and Ronaldo both found the net in a match that also saw Higuain see red against his parent club.
We say: Juventus 3-1 AC Milan
This has been a one-sided fixture over the last eight years, though Milan did come out on top the last time the sides met in this competition. Still, Juve have been a dominant force once again in 2018-19 and are strong favourites to begin the New Year with an eighth Supercoppa Italiana crown, moving them one in front of the Rossoneri as the competition's most successful club.