Aiming to secure their place in the Coppa Italia quarter-finals, AC Milan meet bogey side Sassuolo on Tuesday, as the teams convene for a last-16 contest.
Before dropping down to Serie B, the Neroverdi stunned Milan at San Siro more than once, and they will now hope to cause a cup shock.
Match preview
Beaten by local rivals Atalanta BC in last year's quarter-finals, Milan continued an underwhelming record in Italy's national cup, with the Lombardy giants' sole success in almost half a century coming back in 2003.
The Rossoneri also came up just short in 2016 and 2018 - losing finals to Juventus on both occasions - but they will seek a triumphant conclusion to this season's campaign, as they enter at the last-16 stage due to their obligations in Europe.
After posting a third Champions League win on the spin last week, beating Slovan Bratislava 3-2 in Slovakia, Milan moved five points clear of the elimination zone and are occupying a playoff place with three league-phase games to go.
Meanwhile, in Serie A, a Tijjani Reijnders brace boosted their tally to 22 points on Saturday evening, with Alvaro Morata also getting his name on the scoresheet in a dominant 3-0 defeat of Empoli.
Paulo Fonseca's inconsistent side have therefore kept clean sheets in both of their last two home fixtures, since losing 2-0 to Napoli at the end of October.
Still trailing behind the top six, Milan's main hopes of silverware may be restricted to knockout competitions, so Fonseca and co cannot afford to take Sassuolo's challenge lightly.
There have been some spectacular results between the clubs over the past three years, including 3-1 and 5-2 wins for Sassuolo at San Siro and a thrilling 3-3 draw in their most recent meeting, played towards the end of last season.
The Neroverdi's stay among the Italian elite has since been brought to an end, as they failed to address a leaky defence and slipped through the relegation trapdoor.
To spearhead their attempt to bounce straight back, former Lyon coach and 2006 World Cup winner Fabio Grosso was hired, with several key players being persuaded to stay on.
Star man Domenico Berardi is still on the books in Reggio Emilia after overcoming a serious injury, while Norwegian midfielder Kristian Thorstvedt was on target in Friday's 2-0 derby win over Reggiana.
As a result of that latest success, Sassuolo occupy top spot in Serie B, having lost just one game so far this season - putting them on course for a quick return to the top flight.
Grosso's side beat Cittadella in the Coppa Italia's opening round before dumping out Serie A strugglers Lecce in round two, and now they can head for Italy's second city dreaming of causing an upset.
Team News
Given the fixture pile-up that awaits between now and the end of 2024, Milan boss Paulo Fonseca is set to make numerous changes to his team on Tuesday, with England internationals Fikayo Tomori, Tammy Abraham and Ruben Loftus-Cheek all vying for promotion from the bench.
Teenage sensation Francesco Camarda is also likely to see some minutes, and the 16-year-old striker will compete with Abraham to supplant Alvaro Morata up front.
Joining long-term absentees Ismael Bennacer and Alessandro Florenzi on the sidelines, Luka Jovic recently underwent surgery on a chronic groin problem.
Meanwhile, Sassuolo will be without Josh Doig and centre-back Filippo Romagna, the latter of whom was forced off by a muscular injury midway through the first half on Friday; his replacement Cas Odenthal could therefore start in Milan.
Nicholas Pierini or Samuele Mulattieri should lead the Neroverdi's attack, with support from Italy winger Domenico Berardi and French forward Armand Lauriente.
Lauriente scored twice when these teams last met in April, while Berardi was on target in both famous wins at San Siro - in 2021 and 2023.
AC Milan possible starting lineup:
Sportiello; Calabria, Tomori, Pavlovic, Terracciano; Musah, Fofana, Loftus-Cheek; Chukwueze, Abraham, Okafor
Sassuolo possible starting lineup:
Moldovan; Toljan, Muharemovic, Odenthal, Pieragnolo; Thorstvedt, Boloca, Obiang; Berardi, Pierini, Lauriente
We say: AC Milan 2-1 Sassuolo
Sassuolo should cause a potentially makeshift Milan some problems in an intriguing last-16 clash - particularly given their current form and past successes at San Siro.
However, Paulo Fonseca can call upon a talented second string, and the Rossoneri should march on to a quarter-final tie against either Roma or Sampdoria.
For data analysis of the most likely results, scorelines and more for this match please click here.
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