Headline: Milan’s European night exposes a deeper problem as Benfica win at San Siro
SEO title: Milan 0-2 Benfica: Amorim faces growing questions after Europa League defeat
SEO description: Benfica beat Milan 2-0 at San Siro in the Europa League, with Ruben Amorim’s rotated side unable to find attacking rhythm or defensive security.
The old European pictures had been placed carefully around San Siro: Milan’s victories of 1963 and 1990, the presence of José Altafini, and Rui Costa’s pre-match greeting. Benfica, beaten by the Rossoneri in the 1963 European Cup final, arrived for a match rich in memory. By the final whistle, however, the stadium was left with a far less flattering image of the present: Milan beaten 2-0, short of ideas and unable to disguise the concerns that have surfaced across their last two outings.
The coach and the club
Ruben Amorim returned to the Europa League on familiar but uncomfortable ground. He had managed Manchester United in the 2025 final lost 1-0 to Tottenham in Bilbao, and his first European match as Milan coach ended with Benfica becoming the first Portuguese side to win at San Siro against the Rossoneri.
The defeat does not decide Milan’s league-phase position, but it makes the wider question harder to avoid. Milan had offered encouraging signs in their opening two Serie A matches, yet their performance against Lazio and then Benfica suggested a side losing conviction rather than building it. The concern was not simply that Benfica were better. It was that Milan rarely looked like a team with a settled route towards goal.
Amorim made five changes from the side used in Rome, despite Milan having only one league fixture before an extended international break. Christian Pulisic, Moreira, Luka Modric and Adrien Rabiot began on the bench, while Filippo Terracciano and Hutchinson were handed starts. Jashari and Musah formed the midfield pairing.
Benfica coach Marco Silva also altered his selection ahead of next weekend’s meeting with Porto. Vangelis Pavlidis, Schjelderup and Prestianni were initially held back, with Jhon Duran chosen up front. Antonio Conte watched from the stands, while the visiting supporters had briefly removed barriers in restricted sections of their end before stewards restored two of the three affected areas.
Benfica bring clarity to San Siro
Milan had not lost any of their previous six major European meetings with Benfica, recording four wins and two draws. That record was never close to extending. Benfica were compact, purposeful and prepared to attack from the wide areas, while Milan spent too much of the opening half watching possession rather than shaping it.
The home side’s difficulties were visible both with and without the ball. Players often appeared static when a midfielder looked for options, and Jashari was seen urging team-mates to make runs. When Milan did reach the final third, their attacks were generally reduced to Samuel Chukwueze deliveries or passes played into the feet of the attacking midfielders, rather than movements beyond Benfica’s defensive line.
Goncalo Ramos worked hard but repeatedly had to retreat from the penalty area, leaving Milan without a consistent presence near Anatoliy Trubin’s goal.
- Benfica took the lead in the 16th minute. Kaminski advanced down the left between Chukwueze and Terracciano, found Lukebakio, and the winger cut inside before beating Mike Maignan with a left-footed effort.
- Soon afterwards, Sudakov struck the post after Jashari lost possession during Milan’s build-up.
- Milan’s most notable first-half attempts came from distance, as Terracciano tested Trubin and Jashari sent a left-footed shot narrowly over.
- Kaminski made it 2-0 early in the second half, turning in El Karouani’s low ball from close range while Milan’s defence remained set but failed to react.
The second goal was particularly damaging because Milan had begun the second half with more energy. Pulisic replaced Hutchinson, and De Winter then missed an open goal from around ten metres after Milan pressed high and recovered the ball. Yet as the home side started to gain territory, Benfica struck again through Kaminski.
For the first goal, Milan allowed too much freedom on Benfica’s left. For the second, Gila, De Winter and Pavlovic were all in the area but none stopped Kaminski from finishing. It was a defensive sequence that summed up the evening: Milan had numbers in place, but insufficient urgency.
A response without a recovery
Amorim turned to Moreira, Saelemaekers, Gila and Rabiot in search of a response. Saelemaekers made an immediate contribution, carrying the ball with purpose and creating opportunities with his passing. He found Rabiot with a forward ball, though the Frenchman could not produce the final pass, and later sent a driven attempt towards the far corner that Trubin pushed away.
Pulisic had two good chances denied by Trubin, including a first-time shot from inside the area that was too close to the goalkeeper. Rabiot also fired over from 25 metres. Moreira supplied a cross from the left, while a well-weighted Saelemaekers pass released Pavlovic, but Benfica defended the situation.
Ramos never found the moment that Milan required. Benfica’s goalkeeper was tested, but rarely unsettled, and the visitors were able to slow the contest through possession when necessary. Lukebakio also forced a save from Maignan late on.
Milan ended with 58 per cent of the ball and a 7-1 advantage in corners, but Benfica won the contest for intensity, taking 16 tackles to Milan’s seven. Possession and set pieces did not become pressure of sufficient quality.
The next chapter needs substance
There were whistles at half-time, a predictable response to another poor opening period at San Siro. The crowd offered modest applause when Milan emerged with greater pace after the interval, but the revival lasted only until Benfica’s second goal.
Modric, who had not played in the Europa League since scoring for Tottenham against PAOK in November 2011, remained unused. He had been named among the substitutes alongside Rabiot, but Amorim did not call on him during the match.
Benfica left Milan with a deserved victory and with their ideas plainly visible. Milan were left with a result that can still be repaired in Europe, but with a performance that demands a faster answer. A season cannot be defined by one league-phase defeat; it can, though, be shaped by the habits it reveals. At San Siro, Milan showed too little movement, too little defensive attention and too little certainty about how to turn possession into chances.
