AC Milan vs Benfica

Sixteen minutes into Wednesday night at San Siro, the tactical blueprint Ruben Amorim brought to AC Milan collided with the clinical reality of European football. Dodi Lukebakio gathered the ball on the right flank, cut inside a retreating Davide Bartesaghi, and curled a left-footed strike into the bottom corner. That single sequence set the tone for a historic 2-0 Benfica victory, marking the Portuguese club's first-ever competitive win over the Rossoneri.[1][2][3][6]

The Matchday 1 clash of the 2026-27 UEFA Europa League league phase was supposed to be a launchpad for Milan's revamped squad. Instead, it exposed the growing pains of a team struggling to adapt to Amorim's signature 3-4-2-1 system. Despite dominating the ball with 60.4% possession and accumulating 0.96 expected goals to Benfica's 0.64, the hosts were repeatedly undone by Marco Silva's disciplined, counter-attacking setup.[2][3][4]

Benfica arrived in Italy riding a seven-match winning streak across all competitions, and their collective confidence was evident from the opening whistle. Silva rotated nine players from his previous starting XI with an eye on a looming domestic clash against FC Porto, handing starts to former Parma defender Alessandro Circati and playmaker Georgiy Sudakov. The sweeping changes did nothing to disrupt their rhythm.[3][6]

After Lukebakio's 16th-minute opener, the visitors comfortably absorbed Milan's disjointed pressure. The hosts nearly conceded a second in the 24th minute when Ardon Jashari surrendered possession cheaply in midfield, allowing Sudakov to drill a low shot off the base of the post. Milan's best response before the break came via a long-range effort from Filippo Terracciano, which Benfica goalkeeper Anatoliy Trubin easily palmed away.[3][6]

Recognizing the stagnation, Amorim turned to his bench at halftime, introducing Christian Pulisic and Mario Gila. The changes sparked a brief, high-energy resurgence. Koni De Winter found himself with a golden opportunity to level the match just five minutes after the restart, but the center-back sliced his shot wide from eight yards out after good buildup work from Alphadjo Cisse.[3][6]

AI

Benfica punished that profligacy almost immediately. In the 53rd minute, Souffian El Karouani drove down the left flank and drilled a cut-back cross into the penalty area. Jakub Kaminski—who had already provided the assist for the opening goal—met the delivery with a fierce first-time shot into the roof of the net, doubling the advantage and effectively killing the contest.[1][2][6]

From there, Benfica managed the game with veteran poise. Trubin anchored a resolute defense, producing a sharp save down to his left to deny a stinging drive from Pulisic late in the half. Former Benfica striker Goncalo Ramos, now leading the line for Milan, cut a frustrated figure against his old club, failing to hit the target with any of his match-high three shot attempts.[1][2]

For Amorim, the defeat compounds a frustrating start to September. Milan remains winless in three matches following consecutive Serie A draws against Juventus and Lazio. "We are creating more problems for ourselves when we have the ball than when the opponent has it," Amorim told Sky Sport Italia after the final whistle. "We are trying to create the routines to have more possession in the box... but we are not creating, we lack creativity near the box."[2][3]

The result rewrites a long-standing European rivalry. Before Wednesday, Benfica had drawn two and lost four of their six meetings with Milan, including painful defeats in the 1963 and 1990 European Cup finals. Breaking that curse at one of Europe's most intimidating venues signals that Silva's squad is a legitimate threat in this year's tournament.[2][3]

Now, Marco Silva's men sit near the top of the 36-team Europa League table with three crucial away points, carrying immense momentum into their weekend domestic fixtures. Milan, meanwhile, faces an uphill battle to climb into the top eight automatic qualification spots, with their next European test scheduled for October 15 away to Salzburg.[4]