With 66 points from 31 games, the Rossoneri are currently heading towards a second-place finish, which, if accomplished, would be their best finish since the 2011/12 season.
However, inconsistent form in recent weeks has raised questions about their ambitions. The team also ceded top spot in the Serie A table.
Stefano Pioli's men led the race from matchday four to 21, but now find themselves nine points behind city rivals Inter Milan.
Yet, a second-place finish is still achievable, with Juventus also dropping points of late.
More disappointing than Milan's form this calendar year has been Sassuolo's overall campaign.
The Neroverdi have been a pale imitation of their imperious selves, which ripped teams to shreds last year. However, back-to-back victories against Benevento and Fiorentina in their last two games have brought them up to eighth in the table.
AC Milan vs Sassuolo Head-To-Head
In 19 clashes between the sides, Milan have beaten Sassuolo 12 times, while losing on just five occasions.
In the first leg of their clash this season, the Rossoneri sneaked through with a 2-1 victory on the road.
AC Milan Form Guide (all competitions): L-W-D-W-W
Sassuolo Form Guide (all competitions): L-D-L-W-W
AC Milan vs Sassuolo Team News
Alessandro Romagnoli is still recovering from an injury and will be sidelined once again, while Davide Calabria is a doubt.
Much to Stefano Pioli's content, talismanic striker Zlatan Ibrahimovic will return from his suspension. This could see Rafael Leao dropped to the bench once again.
Injured: Alessandro Romagnoli
Turkish international Kaan Ayhan has recovered from COVID-19 and joined the squad, but the Neroverdi fret over the fitness of their top scorers, Domenico Berardi and Francesco Caputo.
Injured: Domenico Berardi and Francesco Caputo
AC Milan vs Sassuolo Predicted XI
AC Milan (4-2-3-1): Gianluigi Donnarumma; Pierre Kalulu, Simon Kjaer, Fikayo Tomori, Theo Hernandez; Franck Kessie, Ismael Bennacer; Alexis Saelemaekers, Hakan Calhanoglu, Ante Rebic; Zlatan Ibrahimovic.
Sassuolo (4-2-3-1): Andrea Consigli; Mert Muldur, Marlon, Gian Marco Ferrari, Georgios Kyriakopoulos; Manuel Locatelli, Pedro Obiang; Filip Djuricic, Maxime Lopez, Jeremie Boga; Giacomo Raspadori.
AC Milan vs Sassuolo Prediction
Zlatan Ibrahimovic's return is the single biggest boost Milan could get, and he'll be crucial in breaking down Sassuolo's fragile defense.
The visitors have found some form lately but don't seem likely to take all three points from the Rossoneri.
Prediction: AC Milan 2-1 Sassuolo