AC Milan begin their Europa League league-phase campaign at San Siro on Wednesday night when Benfica arrive for one of the standout fixtures of Matchday 1.
Rúben Amorim’s Milan are unbeaten through four Serie A matches, although the 2-2 draw at Lazio showed there is still work to do defensively. The Rossoneri were two down at half-time before Diego Moreira’s quick-fire double rescued a point, with Christian Pulisic making an immediate impact from the bench.
Benfica travel in excellent form under Marco Silva. They have won nine of their last 10 competitive matches, scored 35 goals in that run and arrive after a 3-1 comeback win over Gil Vicente. Vangelis Pavlidis and Gianluca Prestianni are giving the Portuguese side real firepower.
Still, AC Milan at home is different. San Siro should give Amorim’s new side an extra lift in their first European game of the season, and Benfica’s uncertain right-back situation could be a useful area for Milan to target. Our prediction is AC Milan 2-1 Benfica, with AC Milan to Win at odds of 2.10 our best bet.
Quick Prediction
Best Bet: AC Milan to Win
Market: Match Winner
Correct Score Prediction: AC Milan 2-1 Benfica
Odds: 2.10
Confidence: ⭐⭐⭐☆☆
Expected Goals: Over 2.5 Goals
Both Teams To Score: Yes
📅 Date: 16 September 2026
🏟️ Venue: San Siro
🏆 Competition: Europa League
Match Preview
This is the first of eight league-phase games for both clubs, so there is no need for either side to settle for a passive start. Milan have four home fixtures in the new Europa League format and will see this as an opportunity to put early points on the board in front of their own supporters.
Amorim has used a 3-4-2-1 throughout Milan’s opening Serie A run. His side have taken eight points from four matches, beating Torino and Venezia before drawing with Juventus and Lazio. Those draws away from home were respectable, but the Lazio performance was a reminder that the new system has not fully clicked without the ball. Milan were exposed down their left before the interval and needed Mike Maignan to make several important saves.
The reaction in Rome was far more encouraging. Pulisic, Moreira and Yunus Musah came on at half-time, Milan pressed with more energy and played much closer to the front foot Amorim wants. Moreira struck twice within two minutes, while Pulisic supplied the cross for the first goal. That second-half display gives a strong indication of the XI Milan could use against Benfica.
Gonçalo Ramos remains the focal point up front after starting all four league matches. Behind him, Pulisic and Alphadjo Cissé can find pockets between Benfica’s midfield and defence, while Moreira and Samuel Chukwueze have the pace to stretch play from the wing-back positions. Adrien Rabiot and Musah should be important in the middle, particularly when Milan need to stop Benfica building attacks through Enzo Barrenechea and Leandro Barreiro.
Benfica are not arriving in Milan to sit back. Marco Silva’s 4-2-3-1 has been productive from the start of the campaign, with the team second in Portugal after six league matches on 16 points. Their 21 league goals tell the story, while the Europa League place was secured with a 6-2 aggregate win over Aarhus.
Pavlidis leads the line and comes into this game after scoring twice against Gil Vicente. Prestianni has been even more eye-catching, with eight goals and two assists in 10 matches, and he has scored in each of Benfica’s last three league fixtures. Rafa Silva can drift inside from the right, while Andreas Schjelderup gives Benfica direct running and delivery from the left.
That attacking quality means Milan cannot expect an easy night. Benfica have scored 18 goals across their last five away matches and have looked particularly dangerous when their wide players get isolated against full-backs. The visitors also have depth in João Palhinha, Fredrik Aursnes, Claudio Echeverri, Dodi Lukébakio and Jhon Durán, although Sunday’s trip to Porto is an obvious scheduling complication.
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Why AC Milan to Win Makes Sense
Benfica’s form deserves respect, so this is not a case of ignoring the visitors. They have been scoring freely and Pavlidis, Prestianni and Rafa have enough quality to punish any loose Milan defending. But from a betting point of view, 2.10 is a fair price on Milan at San Siro.
Milan have already shown they can respond when a game turns against them. All seven of their Serie A goals this season have come in the final 30 minutes, which points to a side that can raise its level late on rather than one that fades. Amorim’s changes at Lazio also looked purposeful rather than desperate: Pulisic added craft, Moreira offered penetration and Musah brought athleticism to midfield.
The home angle matters. Milan’s only competitive game at San Siro this season ended in a 2-0 win over Venezia, their only clean sheet of the campaign. Benfica have been excellent away, but this is a considerable step up from several of their recent domestic opponents and it comes in the middle of a demanding spell before Porto.
There is also a possible mismatch on Benfica’s right. Alexander Bah is still uncertain after a shoulder problem, and teenager Daniel Banjaqui has started the last two league games in his absence. Moreira’s momentum, combined with Pulisic’s movement inside, could make that channel a key part of Milan’s plan.
The risk is clear: Benfica have enough pace and goals in their attack to score, especially if Milan leave space either side of their back three. That is why Both Teams To Score is a sensible alternative. Yet Milan have more than enough attacking options to edge a game that should be open, and the straight home win is worth backing at this price.
- ✓AC Milan are unbeaten in four Serie A matches under Rúben Amorim.
- ✓Milan have scored all seven of their Serie A goals this season in the final 30 minutes.
- ✓Benfica have won nine of their last 10 competitive matches.
- ✓Benfica have scored 35 goals across their last 10 competitive fixtures.
- ✓Benfica have scored 18 goals in their last five away matches.
- ✓Gianluca Prestianni has eight goals and two assists in 10 matches.
- ✓Benfica have never beaten AC Milan in previous official meetings.
- ✓Milan won the most recent San Siro meeting 2-1 in 2007/08.
Team News
Milan had a full squad available before the Lazio match and have no confirmed injury, suspension or Europa League registration absence for this fixture. Pulisic returned after being managed early in the season and his assist in Rome puts him in contention to start. Moreira’s two goals should also earn him a bigger role, while Musah is a strong candidate to return to midfield. Amorim may rotate in the back three, where Matteo Gabbia and Fikayo Tomori are available options.
Benfica’s main concern is Bah. The right-back missed the last two league matches while recovering from a shoulder injury and could face a late fitness call. Banjaqui has been fit enough to deputise, but Bah’s availability would give Silva more experience in a difficult away fixture. Bruma is not in Benfica’s Europa League squad, while there are no confirmed suspensions.
Possible Starting Lineups
AC Milan Possible XI
Maignan; Gila, Gabbia, Pavlović; Chukwueze, Musah, Rabiot, Moreira; Pulisic, Cissé; Gonçalo Ramos
Benfica Possible XI
Samuel Soares; Banjaqui, Tomás Araújo, Lenglet, Dahl; Barrenechea, Barreiro; Rafa Silva, Prestianni, Schjelderup; Pavlidis
Players to Watch
Diego Moreira — AC Milan
Moreira changed Milan’s last match with two goals from the left after coming on at half-time. If he starts as the attacking wing-back, his running can push Benfica’s right side backwards and create room for Pulisic closer to Ramos.
Christian Pulisic — AC Milan
Pulisic needed only one half against Lazio to make a mark, setting up Moreira with a precise cross. His ability to receive between the lines could be especially important against Benfica’s double pivot.
Vangelis Pavlidis — Benfica
Pavlidis is Benfica’s main penalty-box threat and arrives after a two-goal display against Gil Vicente. Milan’s centre-backs must be alert to his movement when Rafa and Prestianni attack from wide areas.
Gianluca Prestianni — Benfica
Prestianni is in exceptional early-season form and has scored in three successive league games. His pace and willingness to drive inside make him Benfica’s most dangerous counter-attacking weapon.
Head-to-Head
Benfica have never beaten AC Milan in their previous official meetings. Milan’s overall record is five wins and two draws when Latin Cup matches are included.
The most recent meetings came in the 2007/08 Champions League group stage, when Milan won 2-1 at San Siro before drawing 1-1 in Lisbon. Benfica also lost their previous European visit to Milan, going down 2-0 in the 1994/95 Champions League quarter-finals.
Final Verdict
Benfica’s recent numbers are hard to ignore and they should create chances through Pavlidis, Prestianni and Rafa. Milan’s defensive work remains a concern after conceding in each of their last three league games.
However, this looks like the right time to side with Milan at home. Amorim has attacking options in form, Pulisic’s return adds quality around Ramos and Moreira can exploit Benfica’s uncertainty at right-back. At 2.10, AC Milan to Win is the best bet, with a competitive 2-1 home win the correct-score prediction.
FreeOddsTips Prediction
Benfica should make this a proper test, but Milan can use the San Siro crowd and their improved attacking balance to get the better of the Portuguese side. The visitors are capable of scoring, yet Milan have enough quality in the final third to come through a close contest.
Best Bet: AC Milan to Win
Odds: 2.10
Confidence: ⭐⭐⭐☆☆
Correct Score: AC Milan 2-1 Benfica
