AC Milan and Benfica will renew one of European football’s most storied rivalries on Wednesday when the two former continental champions meet at the iconic San Siro Stadium to open the 2026/27 UEFA Europa League group stage. For the host Rossoneri, securing direct qualification for the group stage represents a modest position for a club accustomed to competing for the Scudetto, yet expectations inside the camp remain uncompromisingly high. Manager Ruben Amorim, who previously guided Manchester United to the 2024/25 Europa League final before falling to Tottenham, made his ambitions explicit ahead of Wednesday’s clash. Stating clearly that Milan’s primary objective is to win the entire competition, Amorim arrives with unfinished business in Europe and a squad seeking to re-establish its continental dominance.
Milan enter this opening match on a solid run of form, remaining unbeaten in their last five matches with three victories and two draws. That streak kicked off with an emphatic 4-2 win over Manchester United in their final preseason fixture, though recent domestic outings have proven more tight, capped by a 2-2 draw against Lazio that marked two straight draws for the Italian side. Offensively, the Red and Black have been consistently active in front of goal, with fewer than two goals occurring just once across their previous five matches. Amorim’s side now aims to convert their domestic resilience into full points on the European stage against a potent Portuguese opponent.
Benfica arrive at San Siro posing a formidable threat of their own, having recently defeated Danish outfit Aarhus in the playoff round at the Estádio da Luz on August 20 to earn their place in the group stage. The Eagles have showcased staggering attacking output under European lights, scoring at least two goals in nine of their last ten home matches in the Europa League. Furthermore, total goals have surpassed 3.5 in eight of Benfica’s past ten fixtures overall, and they have seen fewer than three total goals only once across their last five games. With both sides demonstrating relentless attacking tendencies, the San Siro curtain-raiser promises high-intensity, end-to-end action between two European heavyweights.
Wednesday’s collision forms part of a fascinating wider Europa League landscape across the continent. The competition features intriguing matchups elsewhere, including Sunderland marking their first European campaign since 1973 with upcoming trips to San Siro alongside a home clash against AZ Alkmaar at the Stadium of Light. Meanwhile, Anderlecht prepare to host Lyon at Lotto Park with both teams riding three-match unbeaten runs, while Bournemouth, Crystal Palace, and Scottish Premiership champions Celtic navigate demanding slates. Celtic dropped into the competition after surrendering a four-goal lead to LASK in their Champions League play-off tie and now prepare to face Marseille, Besiktas, and Benfica.
As San Siro prepares for Wednesday’s opening kickoff, the pressure rests heavily on Amorim’s shoulders to deliver on his ambitious declarations. Facing a Benfica squad that routinely pushes the tempo and produces high-scoring affairs, Milan must tighten up a backline that recently conceded twice against Lazio if they are to secure all three points. With a long campaign ahead that includes potential traps against dynamic opposition, setting the tone on matchday one is paramount for the Rossoneri as they launch their quest for European silverware.
