The Viola's general manager passed away after falling ill just before their game against Atalanta BC, which was then postponed, and they may soon be on the hunt for a new head coach; Milan, meanwhile, are focused on securing a top-two finish.
Match preview
Just ahead of their final fixture before the international break, Fiorentina found themselves facing an unfolding tragedy, and their contest with Atalanta was called off at the last minute: general manager Joe Barone was rushed to hospital in nearby Milan, but later passed away.
Following a fortnight of reflection, news has emerged that coach Vincenzo Italiano may move on when his contract expires at the end of the season, leaving Viola president Rocco Commisso with a rebuild on his hands this summer.
With one point from their most recent domestic outing, a 2-2 draw at home to Roma, Italiano's side have secured 27 from a possible 42 on offer at Stadio Franchi so far, but they now return to action with a tough contest against Serie A's second-placed side.
Lacking a prolific striker since the departure of Dusan Vlahovic two years ago, Fiorentina's last 10 league goals have been scored by 10 different players, while Antonin Barak found the net in their recent Europa Conference League draw with Maccabi Haifa, which secured aggregate victory and a place in the quarter-finals.
Failing to finish off their opponents has proved costly of late, as the Tuscan club have also drawn three of their last four league games, so they will hope to find a more ruthless edge during an upcoming flurry of fixtures.
In addition to taking on Viktoria Plzen in a two-legged Conference League tie, Fiorentina are semi-finalists in the Coppa Italia for a second season running - they meet Atalanta next week, between challenging games against Milan and Juventus.
When they last met the Viola in November, Milan ran out 1-0 winners at San Siro, as Theo Hernandez scored the only goal with a spot-kick just before half time.
Since then, the Rossoneri have experienced highs and lows - recovering from a mid-season stumble in Serie A but exiting both the Champions League and Coppa Italia. However, beating Hellas Verona just before international football intervened helped them tighten their grip on second spot in the standings.
One of three Milan scorers at Stadio Bentegodi, American winger Christian Pulisic has already equalled his best season in terms of league goals and is now just one shy of reaching double figures for the very first time.
Pulisic is very much part of Stefano Pioli's favoured front three, also featuring Olivier Giroud and Rafael Leao, but Milan have also scored more times via substitutes than any other team throughout Europe's top five leagues this season - a tally of 14 is the club's best so far this century.
Such squad depth could aid their Europa League run, in which Italian counterparts Roma await in the quarter-finals, but the Scudetto is surely out of reach for another year.
The Rossoneri trail city rivals Inter Milan by 14 points, but claiming runners-up spot ahead of Juventus would still represent a minor achievement: no team has gained more points (15) or scored more goals (15) away from home in 2024, so they will be confident of increasing those tallies this weekend.
Fiorentina Serie A form:
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Fiorentina form (all competitions):
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AC Milan Serie A form:
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AC Milan form (all competitions):
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Team News
Milan may call upon Davide Calabria and Alessandro Florenzi to fill their full-back positions on Saturday evening, as Theo Hernandez must serve a suspension for accumulated bookings.
Over the past two seasons, the Rossoneri have won 64% of matches with Hernandez in the starting XI, compared to 22% without him; their average output also drops significantly - to just one point and 0.8 goals per game.
Pierre Kalulu is still injured, while Simon Kjaer picked up a knock on Denmark duty, so Fikayo Tomori and Mattia Gabbia should be partnered at the heart of a back four selected by former Fiorentina boss Stefano Pioli.
Starting up front, Olivier Giroud is Milan's leading scorer on 12 league goals, which sees him tied for third in the Capocannoniere rankings; recent rumours suggest the French forward could be bound for MLS later this year.
Joint-top scorer for Fiorentina this term, alongside ex-Milan midfielder Giacomo Bonaventura, Nico Gonzalez has already equalled his best goal return in a Serie A season; however, he has scored just once in his last 10 league appearances after netting six times across the first 11.
Bonaventura will miss this meeting with his former club due to a one-match ban, so either Antonin Barak or Lucas Beltran is set to start behind on-loan striker Andrea Belotti.
If back-up goalkeeper Oliver Christensen is passed fit, Viola boss Vincenzo Italiano will have a full squad available to him.
Fiorentina possible starting lineup:
Terracciano; Kayode, Milenkovic, Ranieri, Biraghi; Arthur, Mandragora; Gonzalez, Beltran, Sottil; Belotti
AC Milan possible starting lineup:
Maignan; Calabria, Tomori, Gabbia, Florenzi; Bennacer, Reijnders; Pulisic, Loftus-Cheek, Leao; Giroud