AC Milan vs Benfica Betting Tips & Preview

Benfica to win

Benfica head to the San Siro on the back of a run of form that simply outshines their hosts, and that's the main reason for siding with the Portuguese side in this Europa League League Stage fixture. AC Milan have shown flashes of quality but have also drawn back-to-back games and lost their most recent completed outing before that, while Benfica have won every single one of their last five matches without exception. Our model puts Benfica's win probability at 43.9%, comfortably the most likely single outcome across the market, and that's the basis for the pick rather than anything to do with the odds on offer. The 3.35 price is simply what's available should you want to back it — the selection stands on the strength of Benfica's momentum and Milan's patchier recent output, not on any perceived gap between our number and the bookmakers'.

Recent Form

AC Milan's last five fixtures paint a mixed picture. They were beaten by Cagliari back in late May, then bounced back with wins over Torino and Venezia either side of the turn of the season, before drawing consecutive games against Juventus and Lazio in early September. Two draws on the spin against decent domestic opposition suggest a side that's competitive but not currently firing on all cylinders, and there's no evidence in this data of the kind of ruthless streak that wins knockout European ties.

Benfica, by contrast, arrive in outstanding touch. AGF, Estoril, Marítimo, Moreirense and Gil Vicente have all been beaten in succession across late August and into September, giving them a perfect five-from-five record heading into this trip to Milan. That's about as strong a platform as any side could hope for going into a European away fixture, and it's difficult to ignore when weighing up the two teams' trajectories right now.

Head-to-Head

History between these two clubs is sparse based on what's on record, with just two meetings listed, both dating back to 2007. Milan won the first of those, a home fixture in September of that year, before Benfica levelled the ledger with a draw in Lisbon that November. Overall that leaves the head-to-head record at Milan 0-1-1 Benfica from Milan's perspective across those two games — effectively honours even, with Milan yet to taste victory over Benfica across the two recorded encounters. It's a thin sample and nearly two decades old, so it shouldn't carry much weight in isolation, but it does at least confirm this has been a competitive fixture whenever the two have crossed paths before.

Team News

There are no players listed as sidelined for AC Milan in our data, so on paper they should be able to select from a full-strength squad for this one. Benfica have two absentees on record: Gianluca Prestianni, out since late September 2025 due to a national team call-up, and Gonçalo Oliveira, sidelined since mid-May 2026 with an unspecified injury. Neither is described as a guaranteed starter in the information available, so it's hard to say how significantly either absence dents Benfica's options, but it's worth flagging that they aren't going into this match with a completely clean bill of health, even if Milan's situation looks tidier on the face of it.