The most electric night in Milan is set for November 23, 2025 — not just another match, but a defining moment in the Derby della Madonnina. At Stadio San Siro, Inter Milan and AC Milan will clash with the top of Serie A hanging in the balance. Kickoff is 20:45 CET, with Marco Sozza refereeing and Gianluca Aureliano overseeing VAR. This isn’t just a rivalry game — it’s a power shift waiting to happen.
Why This Derby Feels Different
Inter, the Nerazzurri, are flying. After 11 league matches, they’ve scored 26 goals — eight more than any other team in Serie A. They’ve won their last three matches, all at San Siro, and haven’t lost at home since August. Their attacking trio of Lautaro Martínez, Marcus Thuram, and Ange-Yoan Bonny has been unstoppable. Meanwhile, AC Milan, the Rossoneri, sit third — two points behind — after a shock 2-2 draw with Parma, where they blew a two-goal lead. That performance exposed cracks. They’re still unbeaten in the league (only one loss all season, to Cremonese), but their recent form feels fragile.
Here’s the twist: Inter’s dominance isn’t just statistical — it’s psychological. They’ve won seven of their last eight league games. AC Milan? Four draws in their last six. The pressure isn’t just on the pitch — it’s in the dressing room. And it’s not lost on anyone that Massimiliano Allegri, Milan’s manager, has a 16-5-5 record against Inter in his career. But this? This is his first derby as Milan’s boss in over a decade. He knows what’s at stake.
The Managers: Chivu’s Rise vs Allegri’s Legacy
Cristian Chivu isn’t just Inter’s head coach — he’s a club legend. A key part of Mourinho’s treble-winning side in 2010, he returned to the club as a youth coach and now leads the senior team. His side plays with rhythm, intensity, and a terrifying ability to score in the opening and closing minutes of matches — five goals in the first 15 minutes, five in the final 15 plus stoppage time. They don’t just win; they break you.
Allegri, meanwhile, is a master of pragmatism. His Milan side has made the fewest substitutions in Serie A this season — just 39 in 11 games. That’s discipline, yes — but also risk. He’s banking on experience over rotation. And he’s right to be confident: November is his best month. In 66 November matches as a manager, he’s won 44, drawn 14, lost only 8. That’s 2.21 points per game. But can history repeat? Inter’s current form says no. Allegri admitted as much: “They’re favorites. But that doesn’t mean we don’t have a chance. Quite the opposite.”
The Players Who Could Decide It
Lautaro Martínez is priced at 4/1 to score first — and for good reason. He’s been clinical. But don’t sleep on Rafael Leao. The Portuguese winger has been Milan’s spark — and he’s hungry. He scored in the Parma draw, and with Christian Pulisic and Adrien Rabiot back in midfield, Milan’s attack looks sharper. Rabiot’s return could shut down Inter’s counterattacks — the very weapon that’s buried so many teams this season.
Inter’s defense, however, has been rock-solid. Only one clean sheet missing since August. But here’s the oddity: five of Milan’s last seven games have seen goals from both teams. And Inter? They’ve scored in all 15 competitive matches this season — 37 goals total. If both teams find the net, it’s a shootout. And that’s exactly what the bookmakers expect. Both teams to score? Odds of 8/11. That’s not a gamble — it’s a forecast.
Predictions: Who’s Right?
The analysts are divided. Sports Mole predicts a 1-0 Inter win — “Milan can’t afford to fall five points behind,” they write. SempreMilan.com counters with a 2-1 Milan victory, betting on Leao and Pulisic to exploit Inter’s high line. Football Whispers and Sportskeeda both lean toward a 2-2 draw. And here’s why that’s plausible: Inter’s last five derbies? They’ve lost three. The February 2025 meeting ended 1-1, only saved by a late Stefan De Vrij header. That’s not fluke — that’s pattern.
And the betting markets agree. Inter at 19/20 (1.95) to win. Milan at 3/1 (4.00). Draw at 5/2 (3.50). The odds say Inter should win. But football doesn’t care about odds. It cares about heart, timing, and that one moment — the pass, the touch, the rebound — that changes everything.
What’s at Stake Beyond the Table
This isn’t just about points. It’s about identity. Inter’s fans believe they’ve returned to their dominant era. Milan’s supporters cling to the belief that their club still carries the soul of European football. A win for Inter would push them to a five-point lead — a psychological chasm. A win for Milan? It would breathe life into their title hopes and silence the doubters.
And then there’s San Siro — the cathedral. The roar when the teams emerge. The silence when the ball hits the net. The way the city holds its breath. This match will be remembered. Not just for the scoreline, but for the way it shifts the narrative of the entire season.
What’s Next?
If Inter wins, they’ll be in full control of the title race. Their next three matches — against Lazio, Fiorentina, and Bologna — look manageable. If Milan wins? The table turns. Roma, sitting level on points with Inter, will smell blood. And the derby becomes a turning point, not just a fixture.
Either way, the winner will carry momentum into the winter break. The loser? They’ll have to rebuild belief — and fast.
Frequently Asked Questions
How does this match affect Inter Milan’s title chances?
A win would extend Inter’s lead to five points over AC Milan and put them six ahead of Roma — effectively putting them in the driver’s seat for the Scudetto. With 26 goals in 11 games, they’re the league’s most potent attack, and their unbeaten home record since August makes San Siro a fortress. Losing, however, would open the door for Roma and keep the race wide open.
Why is Allegri’s November record significant?
Massimiliano Allegri has a 44-14-8 record in November across his managerial career, averaging 2.21 points per game — the best monthly performance of his tenure. That’s why Milan fans are hopeful. But this is his first derby as Milan boss in over 10 years, and Inter’s current form is unlike any he’s faced before. History helps, but momentum matters more.
What’s the historical trend in recent derbies?
Inter have lost three of their last five league derbies against AC Milan, including a dramatic 1-1 draw in February 2025 that required a late Stefan De Vrij goal. In five of Milan’s last seven matches, both teams scored. That pattern — high scoring, late drama — is likely to repeat. The last five derbies have seen an average of 3.2 goals per game.
Why is AC Milan making so few substitutions?
AC Milan has made just 39 substitutions in 11 Serie A matches — the fewest in the league. Allegri believes in continuity and chemistry over rotation. But it’s risky: fatigue sets in, especially in high-intensity derbies. Inter, by contrast, has rotated more, keeping their squad fresh. That could be decisive in the final 20 minutes.
Who’s the key player to watch on the night?
Lautaro Martínez is the obvious pick — 11 goals in 11 league games, and Inter’s most reliable finisher. But Rafael Leao might be the game-changer. His pace can break Inter’s high line, and with Pulisic and Rabiot supporting, Milan’s attack could be more dangerous than the stats suggest. If Leao scores early, the entire stadium flips.
Can AC Milan actually win this derby?
Absolutely. Inter may be favorites, but derbies aren’t won by tables — they’re won by moments. Milan have beaten Inter at San Siro before under Allegri (in 2021), and their recent form shows resilience. If Rabiot controls the midfield and Leao exploits space behind Inter’s fullbacks, a 2-1 or even 3-2 win is possible. The odds may favor Inter, but passion doesn’t follow probabilities.