Milan Falls Apart at San Siro: Amorim Gets It All Wrong, Benfica Wins 2-0

Milan had a disastrous night at San Siro, where Benfica won 2-0 without the Rossoneri ever really giving the impression that they could turn around a night that started badly and ended even worse. Several lineup choices made by Ruben Amorim backfired: goals by Lukebakio in the 16th minute and Kaminski in the 53rd minute both came after individual or team errors. The Lisbon side handed the Rossoneri their first loss of the season; they’ll return to the field in a month in Salzburg knowing they absolutely must win.
Amorim surprised everyone even before the opening whistle, fielding Filippo Terracciano to round out the defensive trio alongside Koni De Winter and Strahinja Pavlovic: the former Verona and Cremonese player hadn’t started for Milan since December 29, 2024. In midfield, Jashari got the nod, but a turnover by him allowed Sudakov to get a shot off that hit the post. Benfica had already taken the lead in the 16th minute, thanks to a solo run by Lukebakio that caught Bartesaghi off guard, and even Jashari himself seemed rather distracted.
Right from the start of the second half, Amorim tried to turn things around, leaving Terracciano and Hutchinson on the bench and replacing them with Pulisic and Gila. Unfortunately, Gila ended up contributing to Benfica’s second goal, scored in the 54th minute by Kaminski, with the former Lazio player standing motionless—just like Pavlovic and De Winter. The Belgian, incidentally, had made a name for himself a few minutes earlier by blasting an easy tap-in high over the bar following a shot by Cissé—once again one of the few bright spots for a Milan side that remains far from the high standards hoped for this summer.
Amorim’s shortcomings became even more apparent as the match drew to a close: among Milan’s best chances in the second half were the two set up by Pulisic—who, as mentioned, had initially been left on the bench—and a few runs by Saelemaekers. Saelemaekers, for his part, had only entered the game around the one-hour mark, replacing Bartesaghi. In the first half, only Terracciano—with a long-range shot—and Jashari from the edge of the box a few minutes before halftime had tried their luck.
A bitter evening that clashes with the ambitions declared by Amorim himself on the eve of the match. The Portuguese coach, at a press conference, had raised the bar in no uncertain terms: “I want to take Milan all the way, at least to the final,” he had said, adding that “every competition must be played with the goal of winning it.” Those words now risk backfiring, in light of a performance that highlighted defensive fragility and a worrying lack of cohesion—especially against an opponent, Benfica, whom Amorim knows well from his playing days and his connection to President Rui Costa.
It must be said that the decision to field a largely reshuffled lineup had been announced and partly justified by the need to conserve energy ahead of league matches. The Rossoneri bench, packed with quality players such as Modric, Rabiot, Saelemaekers, and Loftus-Cheek, attests to the depth of a roster built to compete on multiple fronts. However, the management of the defense remains an open question: behind the starting trio of Gila, De Winter, and Pavlovic, the alternatives are limited, and Terracciano’s performance certainly did nothing to dispel doubts about this area of the field.
The loss to Benfica comes at a time when things weren’t exactly going great for the Rossoneri, who were coming off two consecutive league draws against Juventus and Lazio. In the standings, Milan is among the teams tied for fourth place with 7 points, trailing Roma, Inter, and Lazio itself—one of the surprises of this early season. The European defeat therefore risks further dampening the morale of a team that, after a promising start to the season to say the least, has already seen critics begin to turn up their noses following the dramatic draw with Lazio.
