AC Milan vs Benfica: Champions League Giants Meet in the Europa League
AC Milan will host Benfica at San Siro in the opening matchday of the 2026/27 Europa League on Thursday, September 17, with two European heavyweights meeting in a competition neither club expected to be playing in this season.
Both Milan and Benfica are traditionally associated with the Champions League, but disappointing domestic campaigns in 2025/26 left them outside Europe’s elite competition. They must now begin their continental campaigns in the Europa League as they attempt to rebuild.
Benfica ended last season unbeaten under Jose Mourinho, recording 23 victories and 11 draws. That impressive record, however, was not enough to secure a Champions League place as they finished third in the Primeira Liga behind Porto and Sporting CP.
Portugal were allocated only two direct places in the competition, leaving Benfica to drop into the Europa League despite losing just once throughout the campaign.
Milan endured an even more frustrating domestic season. Rossoneri missed out on European qualification after being overtaken by Como in the closing stages of the Serie A campaign. The disappointment contributed to a major change on the bench, with Ruben Amorim appointed to lead a new project at San Siro.
The Portuguese coach is now tasked with rebuilding a squad featuring several high-profile players, including veteran midfielder Luka Modric. The meeting in Milan should therefore carry significant pressure for both teams. Each side possesses considerable individual quality, with established names spread throughout their squads.
There is also an interesting managerial subplot. Amorim and Benfica coach Marco Silva both worked in the Premier League last season, giving the match another layer of tactical intrigue.
The fixture also marks the first meeting between Milan and Benfica in European competition since 2007. Their most recent encounters came in the Champions League, with Milan winning 2-1 at San Siro before the sides drew 1-1 in Lisbon.
Historical meetings have generally favoured Milan, although Benfica have proved capable of making the contest competitive. With both clubs seeking a strong start to their Europa League campaigns, another closely fought encounter appears likely.
Milan will have home advantage and will hope their attacking quality can prove decisive, while Benfica are expected to rely on their technical ability and combination play to threaten the Rossoneri.
Head-to-Head: AC Milan vs Benfica
- November 28, 2007 — Benfica 1-1 AC Milan | Champions League
- September 18, 2007 — AC Milan 2-1 Benfica | Champions League
- March 15, 1995 — Benfica 0-0 AC Milan | Champions League
- March 1, 1995 — AC Milan 2-0 Benfica | Champions League
- May 23, 1990 — AC Milan 1-0 Benfica | Champions League
Predicted Lineups
AC Milan (3-4-2-1): Mike Maignan; Koni De Winter, Mario Gila, Strahinja Pavlovic; Samuel Chukwueze, Adrien Rabiot, Luka Modric, Diego Moreira; Christian Pulisic, Ruben Loftus-Cheek; Goncalo Ramos
Head coach: Ruben Amorim
Benfica (4-2-3-1): Anatoliy Trubin; Ezequiel Banjaqui, Tomas Araujo, Clement Lenglet, Milos Kerkez; Joao Palhinha, Martin Baturina; Claudio Echeverri, Ianis Hagi, Andreas Schjelderup; Vangelis Pavlidis
Head coach: Marco Silva
Prediction
Both teams have enough attacking quality to produce an entertaining contest, but their recent struggles make this difficult to call. Milan’s home advantage should give them confidence, while Benfica possess enough technical quality to create problems.
A high-scoring encounter with both sides finding the net could be on the cards, with neither team clearly superior.
Prediction: AC Milan 2-2 Benfica.
