Stadio San Siro sets the stage for a handsomely-looking Serie A showdown between early title contenders Milan and out-of-sorts Fiorentina. Despite their visitors’ disastrous league start, the Rossoneri would be naive to take anything for granted.

Milan started the 2025/26 Serie A season with a dismal 2-1 home loss to newly promoted Cremonese. However, returning manager Massimiliano Allegri has since steadied the ship, inspiring his side to five consecutive league matches without losing (W4, D1).

After winning four top-flight outings in a row, Milan slumped to a scoreless draw at Juventus on the eve of the international break. Christian Pulisic squandered a second-half penalty and, thereby, a chance to fire the San Siro giants to the top of the standings before the pause.

Visiting Fiorentina would probably trade places with Milan any day of the week after starting the new season with a whimper rather than a bang. Back to Italian football after a year in Saudi Arabia, Stefano Pioli couldn’t have imagined a worse way to kick off his second tenure in Florence.

Fiorentina have gone winless in all six Serie A matches this season (D3, L3), with only four sides scoring fewer goals than their four pre-round. Despite taking an early lead through Moise Kean in their last league game before the break, La Viola lost 2-1 to Roma at home.

As a result, they spent the two-week hiatus in the drop zone. That’s hardly inspiring ahead of their trip to San Siro.

Allegri has tightened Milan’s backline since that underwhelming defeat to Cremonese. Indeed, the 19-time Italian champions have since only conceded once in five league games. Interestingly, all three goals they’ve shipped this term arrived at San Siro, suggesting there’s still room for improvement.

Though rock-solid in defense, fans would likely appreciate a more clinical Milan, with the Rossoneri scoring 2+ goals in just two of their last four Serie A outings. Yet, even a narrow win would see the Rossoneri extend their unbeaten league run to six matches for the first time since early 2024.

Defensive solidity will undoubtedly be the key, considering six of Milan’s last seven wins have produced a clean sheet. It’s also worth noting that Milan tend to go cagey as the game progresses, as evidenced by the fact they have yet to score beyond the 64th minute at home this season.

Trapped in the relegation zone, Fiorentina can ill-afford more slip-ups if they’re to rekindle their dream of qualifying for European competitions next season. Needless to say, Pioli has already come under heavy scrutiny, especially given his side’s nasty habit of turning leads into unfavorable outcomes.

To put that in perspective, Fiorentina have dropped a league-high eight points from winning positions this season, compared to ten in the entirety of the previous Serie A campaign. That’s not an ideal backdrop for Pioli’s 500th Serie A game as a manager as he takes on a side he led to the Scudetto in 2021/22.

With Fiorentina’s last three Serie A away games ending level, another share of the spoils would see the Tuscan outfit draw four consecutive top-flight matches on the road for the first time since December 2018. Despite drawing 2-2 in this corresponding fixture last term, avoiding defeat at San Siro could be easier said than done.

Indeed, Fiorentina had lost four successive away league encounters against Milan, failing to get on the scoresheet on three occasions.

In addition to long-term absentee Ardon Jashari, Milan will be without Pervis Estupinan, Adrian Rabiot, and Pulisic. Davide Bartesaghi will likely take the Ecuadorian’s place on the left wing, with Samuele Ricci expected to make his first Serie A start for the Rossoneri. Moreover, Rafael Leao has regained full fitness and will join misfiring Santiago Gimenez in the attack.

On the other hand, Fiorentina will take this trip without long-serving forward Christian Kouame and summer signing Tariq Lamptey. Though Kean picked up a minor injury during the international break, the Italian center-forward must grit his teeth and lead the line.

Milan vs Fiorentina Potential Starting Line-ups

Milan (3-5-2): Maignan; Tomori, Gabbia, Pavlovic; Saelemaekers, Fofana, Modric, Ricci, Bartesaghi; Leao, Gimenez.

Fiorentina (3-4-2-1): De Gea; Pongracic, Mari, Ranieri; Dodo, Mandragora, Nicolussi Caviglia, Gosens; Fazzini, Gudmundsson; Kean.

Milan vs Fiorentina Prediction

A gut-wrenching draw in Turin may have taken some wind out of Milan’s sails, but the Rossoneri still have momentum on their side in this clash. The hosts seem in far better shape at the moment and should put three more points on the board.