Read our prediction for AC Milan vs Benfica below. This preview was written by a sport journalist who is specialised in betting tips and predictions.
AC Milan vs Benfica Prediction & Betting tips
AC Milan host Benfica at the San Siro on Wednesday, September 16, 2026, for an opening-round blockbuster in the UEFA Europa League league phase. Both historical European giants find themselves in the Europa League this season, looking to kick off their campaigns with a statement win. AC Milan forward Gonçalo Ramos faces his former club. He will be eager to score his 16th senior goal in UEFA competitions against the side where he made his name. Benfica has won 80% of their last 10 away matches, averaging a staggering 3.6 goals per game on the road. They will test Milan’s backline early. This match marks an intriguing tactical showdown between two relatively new managers—Amorim’s structured 3-4-2-1 system against Marco Silva’s explosive, high-pressing 4-2-3-1.
AC Milan:
Under the management of Ruben Amorim, the Rossoneri remain unbeaten in Serie A with two wins and two draws. They showed tremendous grit over the weekend, fighting back from a 2-0 deficit to draw 2-2 against Lazio. However, defensive vulnerabilities have loomed over their recent outings.
AC Milan (3-4-2-1): Maignan – De Winter, Gabbia, Pavlovic – Chukwueze, Modric, Musah, Moreira – Pulisic, Cissè – Ramos.
Benfica:
Guided by Marco Silva, the Eagles arrive in Milan flying incredibly high on a seven-match winning streak across all competitions. Following a comfortable aggregate victory over Aarhus GF in the playoff rounds, they have been absolutely ruthless domestically, scoring 21 goals in their first six league matches.
Benfica (4-2-3-1): Soares – Banjaqui, Araújo, Lenglet, Dahl – Barreiro, Palhinha – Silva, Prestianni, Schjelderup – Pavlidis.
AC Milan vs Benfica head to head matches
28.07.2019 AC Milan – Benfica 0:1
08.08.2009 Benfica – AC Milan 2:1
28.11.2007 Benfica – AC Milan 1:1
18.09.2007 AC Milan – Benfica 2:1
15.03.1995 Benfica – AC Milan 0:0
* Our advice is: BTS / YES
* Selection odd for this bet is: 1.62
* This analyis is from our perspective and we highly recommend to inform also yourself about all details that can be decisive in your choise to bet!
