The pair met in Serie A at the weekend - with the Rossoneri coming out comfortably on top - and will now battle it out for a place in the cup quarter-finals.
Despite the clubs' proud and illustrious histories, both Milan and their visitors have lifted the Coppa Italia a mere five times apiece.
As a new generation of Rossoneri talent has so far taken the league by storm, this could finally be the season when the Lombardy giants claim the famous old trophy for a first time since 2003.
First, they must repeat the dose against toiling Torino, whose league form suggests that they remain rank outsiders to progress.
The two teams met on Saturday evening at San Siro, with Milan putting their first Serie A defeat of the season - to familiar foes Juventus - behind them with a 2-0 victory decided by strikes from Rafael Leao and Franck Kessie, who reliably scored from the spot.
A relatively regulation win for the injury-hit Diavolo was significantly marked by the return of their towering talisman Zlatan Ibrahimovic in the closing minutes, though midfielders Sandro Tonali and Brahim Diaz sustained injuries during the game - a sure source of concern for head coach Stefano Pioli.
Torino also met Milan, who only now make their entry into the competition due to European participation, in last year's Coppa - at the quarter-final stage - with the Rossoneri again emerging victorious thanks to extra-time goals from Ibrahimovic and Hakan Calhanoglu.
As if another league defeat was not bad enough for under-fire Granata boss Marco Giampaolo - who failed so spectacularly in the Milan dugout after leaving Sampdoria - it emerged after the game that the clubs' directors had met to discuss a deal for his French midfielder Soualiho Meite.
Losing a regular member of the Torino side would prove far from ideal if Giampaolo is to engineer an escape from relegation this term. Furthermore, Meite diplomatically sat out the weekend's loss against his suitors and is likely to do so again on Tuesday.
Il Toro will still hold out hope of an against-the-odds cup success though, as on Saturday former Milan man Ricardo Rodriguez rattled the crossbar with a customary free kick and Milan's indomitable goalkeeper Gianluigi Donnarumma was forced into a sensational save late on to deny Jacopo Segre. Not only that, but Torino surprisingly edged the shots, passing and possession stats too.
Having not won the Coppa since 1993, defensively suspect Torino - who knocked out Serie B sides Lecce and Virtus Entella to make it this far - would dearly love a run to the final this year, but the free-scoring league leaders stand squarely in their way.
Following the weekend action, Giampaolo's men are marooned in the drop zone, with a meagre tally of twelve points and have now failed to win in their last 25 Serie A encounters away to Milan - losing 17 times and even failing to score on 18 occasions.
Torino, therefore, must hope the cup provides some brief respite from their league travails - which could even act as an unlikely spur to their failing form.
AC Milan form (all competitions): DWWWLW
Torino Coppa Italia form: W
Torino form (all competitions): LDDWDL
All eyes will be on the Milan teamsheet, as their expectant tifosi wait to see whether 'King Zlatan' is fit to return to Stefano Pioli's starting lineup. More likely though, the Swedish superstar will begin on the bench again, with the versatile Rafael Leao continuing up front.
Pioli will still be engaged in a spot of crisis management though and is likely to be without the injured Matteo Gabbia, Ismael Bennacer and Alexis Saelemaekers, while Rade Krunic and Ante Rebic are definitely unavailable due to COVID-19.
Sandro Tonali returned from suspension at the weekend but was injured during an incident in which he nearly gave a penalty away, while Brahim Diaz also picked up a knock, but both could be available having trained on Monday. Hakan Calhanoglu was only deemed ready for a few minutes as a substitute at the weekend but may be pressed into service given Milan's mounting midfield absence list.
As on Saturday, Torino boss Marco Giampaolo should have a fully-fit squad to select from, with midfielder Daniele Baselli recently returning from long-term injury. On-loan forward Federico Bonazzoli is a minor doubt though, so may not feature.
In the Granata's familiar 3-5-2 formation, previously ever-present midfielder Karol Linetty is likely to be restored to the first XI - with Milan transfer target Soualiho Meite sitting out - and Simone Verdi favoured to support tireless striker Andrea Belotti up top.
AC Milan possible starting lineup:
Donnarumma; Dalot, Kjaer, Romagnoli, Conti; Kessie, Tonali; Castillejo, Diaz, Hauge; Leao
Torino possible starting lineup:
Milinkovic-Savic; Izzo, Lyanco, Bremer; Singo, Baselli, Rincon, Linetty, Rodriguez; Verdi, Belotti
We say: AC Milan 2-1 Torino
As the weekend's league encounter between these two sides - who have had such contrasting fortunes this year - was a closer contest than many thought, there is a sliver of an opportunity for Torino to trouble injury-hit Milan.
However, with key men Zlatan Ibrahimovic and Hakan Calhanoglu ready to feature for the Rossoneri, expect the home side to progress to the last eight thanks to their greater goal threat.