Football isn't always about the glitz of the San Siro or the heavy weights of the Champions League. Sometimes, it's about a cold Saturday night in Tuscany where things just go sideways. Honestly, if you’ve followed Milan AC vs Empoli over the last few years, you know exactly what I’m talking about. It’s a fixture that looks like a "banker" on paper for the Rossoneri, but usually ends up being a chaotic mess of VAR calls, unexpected red cards, and late-game heroics.
People tend to underestimate Empoli. They see the small stadium—the Stadio Carlo Castellani—and assume Milan will just stroll in and collect three points. But Empoli has this annoying habit (annoying for Milan fans, anyway) of clogging the midfield and turning the game into a physical grind.
What Actually Happened Last Time?
Let’s look at the most recent clash in February 2025. It was a circus. Pure and simple. Milan eventually won 2-0, but that scoreline is a massive liar. It doesn't tell you that Fikayo Tomori got sent off in the 54th minute after a late challenge on Lorenzo Colombo. For a good chunk of the second half, Milan was reeling, playing with ten men and looking like they might actually drop points to a team fighting relegation.
Then the "weird" kicked in.
Luca Marianucci for Empoli decided to retaliate against Santiago Giménez during a VAR check and got himself sent off too. Suddenly it’s 10-on-10. Space opened up, Christian Pulisic started pulling the strings, and Rafael Leão finally broke the deadlock with a header in the 68th minute.
That game also saw a bit of history. Santiago Giménez, the Mexican international, bagged his first-ever Serie A goal to seal the win. He’s the first Mexican to ever score for AC Milan. It’s those kinds of weirdly specific milestones that seem to happen whenever these two play.
The Milan AC vs Empoli Tactical Headache
Why is this game so consistently difficult for the bigger side? Usually, it's down to the tactical setup. Empoli often lines up in a compact 4-3-1-2 or a 4-3-3 that forces Milan's creative players, like Reijnders or Pulisic, to go wide.
- The Middle is a Graveyard: Empoli crowds the central zone. If Milan can’t find Leão on the wing early, they get frustrated.
- The "Ex" Factor: It feels like half the Empoli squad is usually made up of former Milan youth players or loanees. They always have something to prove. Look at Lorenzo Colombo—he hit the woodwork in that last game and nearly ruined Milan's season.
- The Pitch Quality: Let’s be real. The grass at the Castellani isn’t always the carpet of San Siro. It slows the ball down. It suits the underdog.
Milan’s current boss, Sergio Conceição, has had to get creative. In the 2024-2025 season, he basically had to gamble on a triple sub at halftime just to wake the team up. It worked, but it wasn’t pretty.
Head-to-Head: The Brutal Numbers
If you’re a betting person, the history is actually pretty one-sided, despite how "close" the individual matches feel. Out of the last 30 meetings, Milan has won 19. Empoli has only managed 3 wins in that entire span.
- Total Goals: Milan has put 57 past Empoli.
- The Drought: Empoli hasn't beaten Milan since 2017.
That 2017 game was a 2-1 shocker at San Siro. Since then, it’s been a lot of draws and narrow Milan wins. Interestingly, Milan has kept five consecutive clean sheets against them recently. Even when the football is ugly, the defense usually holds firm.
Key Players to Watch in 2026
If these two meet in the back half of the 2025-2026 season, the narrative shifts toward the title race. Milan is currently neck-deep in a five-horse race for the Scudetto. They can't afford a "Tuscan Trip-up."
Rafael Leão remains the X-factor. He’s been bizarrely effective away from home lately. In fact, most of his goals this season have come on the road. Then you have Christian Pulisic. The American has evolved from a "good winger" to the actual heartbeat of Milan’s attack. His ability to provide assists in tight spaces is basically the only reason Milan broke down Empoli's bus last time.
On the flip side, keep an eye on Empoli's youngsters. They keep producing talent. Whether it’s Sebastiano Esposito or guys coming through the ranks, they rely on high-energy pressing. They want to make the game "ugly."
Real Talk: Why This Match Matters for Google Discover
You’re probably seeing this because the next fixture is looming or a major injury just happened. In 2026, the Serie A table is tighter than it’s been in a decade. A 0-0 draw against Empoli isn't just a bad result; it's a season-killer.
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Most fans think the big games—Milan vs Inter or Juve—decide the title. Experts know better. It’s these grind-it-out matches in February and March that actually hand out the trophies.
Actionable Insights for Fans and Analysts
If you are following the next Milan AC vs Empoli match, don't just look at the starting XI. Watch the first 15 minutes. If Milan hasn't recorded a shot on target, they are likely stuck in Empoli's "web."
- Check the Cards: These games get chippy. Expect a high yellow card count.
- The 60-Minute Mark: Milan often struggles early but dominates the final third of the match as Empoli’s fatigue kicks in.
- Watch the Subs: Conceição loves to change three or four players at once if the score is 0-0 at the hour mark.
The best way to prep for the next clash is to track the injury status of Milan’s midfield. Without Reijnders or a fully fit Pulisic, the Rossoneri lack the verticality to pierce a low block. Keep an eye on the official team sheets released an hour before kickoff; if Milan rests their starters for a Champions League tie, an Empoli upset becomes a very real possibility.