Milan's European campaign began in the worst possible fashion on Wednesday night, as Benfica came to San Siro and won with something close to ease, exposing a side that offered almost nothing in attack across 90 minutes.
The result stings on its own, but the circumstances make it worse. According to Gazzetta dello Sport, Benfica made nine changes from their weekend lineup and left star striker Pavlidis on the bench until late in the game, with a top-of-the-table clash against Porto on Sunday clearly the priority. Milan, in effect, lost to a heavily rotated side, and the manner of the defeat left little room for comfort.
Marco Silva set Benfica up in what was nominally a 4-2-3-1 but functioned with far more fluidity than that label suggests. Out of possession, Kaminski dropped from the left into a back five to contain Chukwueze. In possession, Benfica built from a back four, with Lukebakio drifting inside from the right wing into attacking midfield zones rather than hugging the touchline. That movement repeatedly dragged Bartesaghi out of position. Sudakov, meanwhile, shifted from behind the centre-forward Duran over to the left, creating rotations Milan simply could not track.
The contrast with the home side was stark. Gazzetta described Milan as "a team lacking any real identity or substance," and the first half bore that out. The Rossoneri generated almost no attacking cohesion, could not create numerical advantages through their buildup, and resorted to speculative efforts from distance. Hutchinson shooting from range felt like a side out of ideas rather than one choosing its moments.
Benfica's opener arrived through a move that had been telegraphed all half. Lukebakio cut inside from the right, drew Bartesaghi across the edge of the area, and curled a left-footed finish into the corner. Moments later, Sudakov struck the post from a similar area. Milan's best response before the break was a Terracciano strike parried by Trubin, and little else. Gonçalo Ramos, isolated up front, wandered without service, neither sought by his teammates nor able to influence play.
Rúben Amorim tried to change the trajectory at half-time, introducing Gila and Pulisic immediately, then Saelemaekers and Moreira shortly after. De Winter wasted a chance early in the second half, but the brief spark did not catch. Ramos remained anonymous.
The second goal, when it came, summed up the evening. El Karouani delivered a cross that went entirely unchallenged, and Kaminski met it with equal freedom to make it 2-0. Milan's defensive line, according to Gazzetta, resembled "a nativity scene, filled with static figurines."
The final 40 minutes, stoppage time included, produced little beyond a couple of Pulisic efforts from outside the box, one of which tested Trubin. When the only clear chances are long-range shots, the absence of a functioning attacking structure is difficult to hide.
The defeat does immediate damage to Milan's Europa League group standing, but the deeper concern is what it revealed about the squad's cohesion under Amorim. Gazzetta went as far as to question whether even a full-strength Milan side would have fared better given how the night unfolded, and suggested that Conference League ambitions may be a more realistic target than the Europa League itself. Whether Amorim can find the answers before the next European fixture now becomes the pressing question.