AC Milan once again tasted disappointment on a major stage after their journey in the Supercoppa Italiana came to an abrupt end. The Rossoneri were eliminated in the semifinals following a 0–2 defeat to Napoli at Al-Awwal Park, Riyadh, Saudi Arabia, on Friday (December 19, 2025).
The result was particularly painful given Milan arrived as the defending champions. Beyond the scoreline, the loss highlighted a worrying defensive trend that has begun to overshadow the progress made under head coach Massimiliano Allegri in recent weeks.
Napoli proved far more clinical despite Milan enjoying superior possession. David Neres broke the deadlock before halftime, while Rasmus Højlund sealed the victory in the second half with a decisive finish that exposed Milan’s defensive frailties once again.
Tactical Tweaks Fail to Stop Milan’s Slide
Allegri rotated several players in Riyadh, balancing fitness concerns and compensating for injuries to key starters. The Rossoneri began the match in a 3-5-2 system, hoping to maintain defensive stability while controlling midfield areas.
However, after falling behind, Allegri switched to a 4-4-2 in search of greater attacking width. The adjustment brought brief spells of pressure but failed to alter the course of the match. Napoli remained composed, exploiting Milan’s mistakes during transitions and punishing every lapse in concentration.
The defeat extended a worrying pattern: Milan have now conceded multiple goals in three consecutive matches across competitions, a statistic that raises serious questions about their defensive structure.
Red Flags Against Sassuolo and Torino
Milan’s defensive issues were already evident before the Napoli encounter. On December 14, the Rossoneri conceded twice in a home match against Sassuolo at San Siro.
Milan fell behind early after Ismaël Koné scored in the 13th minute. They responded well, with Davide Bartesaghi netting twice in the 34th and 47th minutes to turn the game around. Yet defensive concentration faltered late on, allowing Armand Laurienté to equalize in the 77th minute.
A similar scenario unfolded earlier on December 9, when Milan traveled to face Torino. Defensive lapses saw them concede twice within the opening 17 minutes, with goals from Nikola Vlašić and Duván Zapata.
Milan did show resilience, responding through Adrien Rabiot and a brace from Christian Pulisic. Still, conceding twice so early once again underlined the fragility of their defensive organization.
Rabiot Identifies the Core Problem
Adrien Rabiot did not shy away from addressing Milan’s current struggles. The French midfielder believes the downturn in form stems from a loss of collective compactness rather than isolated incidents.
According to Rabiot, Milan no longer display the same cohesion that characterized their early-season performances. Individual mistakes, particularly at the back, have become increasingly costly.
“We need to regain the compactness and solidity that we’ve slightly lost in the last few matches,” Rabiot told Sportmediaset, via SempreMilan.
Napoli, like several recent opponents, capitalized on Milan’s vulnerabilities during defensive transitions. The lack of coordination between midfield and defense has left gaps that opponents have exploited with ruthless efficiency.
Koni De Winter Under the Spotlight
As Milan search for answers, attention has turned to young defender Koni De Winter, who has found himself repeatedly targeted by opposing attackers.
Against Sassuolo, De Winter struggled to contain Andrea Pinamonti, allowing the forward to act as a focal point in buildup play that eventually led to Laurienté’s goal.
The same issues resurfaced in the Supercoppa clash with Napoli. De Winter was overpowered by Højlund, failing to anticipate the striker’s movement. He was unable to block the decisive pass for the opening goal and later lost a foot race that allowed Højlund to score the second.
While De Winter’s potential remains clear, these recurring moments have intensified calls for Milan to reassess their central defensive options if they are to halt the current trend of goals conceded.
Alarm Bells Ring at San Siro
Three matches, six goals conceded, and elimination from a major competition have triggered alarm bells within the Milan camp. Allegri now faces a crucial challenge: restoring defensive discipline without sacrificing the attacking fluidity that has kept the Rossoneri competitive.
With key fixtures approaching, Milan’s response over the coming weeks could define their season. Addressing structural issues, improving communication at the back, and rediscovering collective solidity will be essential if they are to avoid further setbacks.
For a club of Milan’s stature, defensive instability cannot become the norm. The warning signs are clear—and how the Rossoneri react may determine whether this slump becomes a temporary dip or a deeper crisis..
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