Milan-Fiorentina Preview: Pioli's Birthday Bash

On Monday, Stefano Pioli turns 60. The night before, he will manage his 500th Serie A match as he returns to the San Siro and the handful of players that remain from the team he won the Scudetto with, the one he got tattooed on his arm. In honor of his return, Milan have five players definitely out injured, and one still doubtful as of this writing. And, to make extra special, Milan's Curva Sud will be able to have their flags and banners again at San Siro for the first time in nearly a year, and will be singing in full voice as well. Hopefully, they'll make a banner or sing one more round of "Pioli is on Fire" for the man who managed Milan for nearly five years, even if he went back to his old team now. Hopefully, it will be one to remember for Pioli's Birthday Bash.

How Pioli would probably much rather have celebrated his 60th birthday.

The reality is that Pioli could get sacked as a birthday present. Fiorentina are winless thus far in the league, even if they are doing well in the Conference League. No one knows better than Pioli how difficult it will be to take points from Milan at San Siro, either. Fiorentina's last match was a 2-1 loss to Roma at home. For that match, Pioli lined up a 3-4-2-1 with: De Gea; Pongračić, Pablo Mari, Ranieri; Dodô, Mandragora, Nicolussi Caviglia, Gosens; Fazzini, Guðmondsson; and Moise Kean. While Kean missed playing with Italy over the international break due to an ankle injury, he has been called up amongst Pioli's 24 players for the trip to San Siro. However, Pioli will be missing Koumé and Lamptey to injury.

Smaller team, bigger salaries, but more impacted when injuries hit.

Allegri, on the other hand, tried to downplay the fact that his squad was decimated by their national teams over the break. Huge questions about Deshamps' management of Rabiot and Pochettino's management of Pulisic have arisen as Rabiot comes back from France with... wait for it... a calf injury (at least pretend to be surprised,) and Pulisic has a much more severe hamstring injury that will likely keep him out for at least a month. Neither player will be available on Sunday, nor will Estupiñan, Nkunku, or, of course, Jashari. There are huge doubts as to Loftus-Cheek's availability as well, due to a muscle strain in training, which would make six players out in all, nearly one-third of the tiny squad allotted to Allegri this year.

Good news, though, Saelemaekers made it back from his national team injury in order to train with the team on Friday. And Leão, sent home early from Portuguese national team duty for fitness and having initially trained alone, is also reportedly back to full fitness and scheduled to start this match. The missing players means Allegri will be depriving Milan Futuro of at least Balentien and Sala, even though they are playing a few hours before the first team's match at San Siro. Hopefully, he will be able to scrape together a starting eleven.

Leão could get his first start of the Serie A season on Sunday after being out injured.

Pioli mentioned that Milan had suffered more than their results had shown, which is true. All you had to do was watch the brutal win vs. Lecce or the surprising win with only 10 men vs. Napoli. Pioli probably suffered just like all of us watching those matches, even if they did have happy endings. Likewise, Allegri acknowledged that Fiorentina had put in excellent performances that did not reflect their position on the table. And while that may seem like coaches just playing mind games, both points are actually true this time.

Pioli deserves a birthday gift, and being sacked is certainly not it. If we had to lose to anyone, I couldn't begrudge his happiness (and temporary job security.) But coming into the match with such a beleaguered squad after an international break once again leaves a very bitter taste in the mouth. Particularly when you realize that management seriously shrunk the number of players in the team this season to make it seem like they weren't growing the wage bill (even though they definitely have been.) Not really looking forward to the ominous football part of this match. But seeing and hearing the Curva Sud again will at least make for a festive atmosphere again, and really, that's all you need to make a football match into Pioli's Birthday Bash.

This post inspired by the music of The Cardigans' "Lovefool"

Our next match is:

Campionato Primavera 1 Week 8

Atalanta Primavera vs. Milan Primavera

Sunday, October 19, 2025 • 11:00 CET (5am EDT)

This match is not being televised in the U.S.

Serie D Week 8

Milan Futuro vs. Caldiero Terme

Sunday, October 19, 2025 • 15:00 CEST (9am EDT)

This match should be able to be streamed LIVE on the official Milan App

Serie A Week 7

Milan vs. Fiorentina

Sunday, October 19, 2025 • 20:45 CEST (2:45pm EDT)

In the U.S., this match can be streamed for free on DAZN (in Spanish,) or on Paramount+,

or use a VPN to access better coverage

Serie D Week 7*

Breno vs. Milan Futuro 

Wednesday, October 22, 2025 • 15:00 CEST (9am EDT)

This match is not being televised in the U.S.

*rescheduled due to the  International Break