Momentum and history are pulling in opposite directions at San Siro.

Benfica arrive on the back of a 3-1 win over Gil Vicente, a result that keeps their scoring form ticking over just before the trip to Italy, while AC Milan needed a second-half rescue act just to draw at Lazio in their last outing.

Yet the European ledger between these two clubs still leans heavily towards the hosts, and that tension between recent form and long-term matchup history is exactly what makes this Europa League opener worth a closer look.

Quick Picks

• Our Pick: Double Chance: Benfica And Draw
• Same Game Multi (our combination): Double Chance: Benfica And Draw + 1st Half Over/Under 1.5 Goals: 1st Half Under 1.5 Goals
• Alternative Pick: Both Teams To Score: No

Full markets for this fixture, including the AC Milan vs Benfica odds, are available on Sportsbet, with the individual legs of the combination above listed on that same page.

Milan's Wobble Meets Benfica's Momentum

Milan's most recent performance told two different stories in one match. They fell 2-0 behind at Lazio before substitute Diego Moreira turned the game on its head, scoring in the 65th and 67th minutes to salvage a 2-2 draw.

It was a display that showed character off the bench, but also exposed a defence capable of conceding twice in a matter of minutes, a habit that could prove costly against a Benfica side that has been scoring freely in Liga Portugal.

For additional context, Sportsbet has a separate guide covering UEFA Europa League betting.

This is Matchday 1 of the Europa League's 36-team league phase, where each club plays eight different opponents before the top eight advance directly to the round of 16 and the sides ranked ninth to 24th are routed into knockout play-offs.

Every point matters early, which adds extra edge to a fixture between two clubs with serious European pedigree.

• Date: Thursday 17 September 2026
• Kick-off: 5:00 am AEST
• Local Kick-off: 9:00 pm CEST
• Venue: San Siro, Milan, Italy

How to watch AC Milan vs Benfica in Australia

Australian viewers can catch this one live on Stan Sport, which holds exclusive rights to every Europa League match live and on demand, with coverage building into the 5:00 am AEST kick-off on Thursday 17 September.

AC Milan vs Benfica Prediction

Backing Benfica And Draw leans on genuine substance: a 3-1 win to close out their domestic campaign against a Milan side still shaky enough to concede two goals inside a half at Lazio.

History pushes back hard, though, with Milan unbeaten in six previous continental meetings between these clubs, winning four, including two European Cup finals, and holding home advantage at San Siro.

For more background, Sportsbet has a separate guide covering 3-4-2-1 formation.