AC Milan vs Benfica Prediction & Betting Tips (16 September)

AC Milan host Benfica at San Siro on Wednesday 16 September 2026 in a standout 2026/27 UEFA Europa League league-phase opener, with Rúben Amorim’s rebuilt Rossoneri taking on Marco Silva’s in-form Eagles in one of the round’s most tactical matchups. European odds have made Milan a narrow home favorite at about 2.18, the draw is close to 3.80, and Benfica are around 3.47, but the market price still undervalues Milan’s San Siro edge in a game our prediction settles at 2:1 for the Italian side.

Milan arrive unbeaten in Serie A after early-season tests, showing resilience in a 1-1 draw at Juventus and control in a 2-0 win over Venezia, with a 2026/2027 squad built around Mike Maignan in goal, Pervis Estupiñán, Strahinja Pavlović, Mario Gila and Koni De Winter across the back, Luka Modrić, Adrien Rabiot and Yunus Musah in midfield, and Christian Pulisic, Alexis Saelemaekers, Samuel Chukwueze and Gonçalo Ramos providing the decisive attacking thrust.

Benfica’s route into the league phase was emphatic after qualifier wins over St. Gallen, Hearts and AGF, and their domestic form has carried that momentum through a 0-3 victory at Marítimo and a 2-1 home success against Estoril, with Anatoliy Trubin or Samuel Soares behind Tomás Araújo, Clément Lenglet, Alexander Bah and Samuel Dahl, João Palhinha and Leandro Barreiro screening Heorhiy Sudakov, while Rafa Silva, Gianluca Prestianni, Vangelis Pavlidis, Jhon Durán and Dodi Lukébakio give the Eagles real transitionspeed.

The key battle is Milan’s patient positional play against Benfica’s counter-pressing and direct runs in behind, and if Modrić and Rabiot can slow the game early, Milan’s wider rotations and set-piece pressure should create enough high-value chances to edge it; expect Benfica to threaten on the break and make the final quarter tense, but our final call for this Europe - Europa League clash is AC Milan 2:1 Benfica, a result that would give Amorim’s new-look 2026/2027 squad an important home statement to begin the league ph