- 1 AC Milan vs Benfica : 11 unbeaten for one side, fifth place that cost dearly for the other
- 2 AC Milan : back-to-back draws and a Diego Moreira brace to rescue the Olimpico
- 3 Benfica : Pavlidis and Prestianni lead the most productive attack in the field
- 4 Europa League prediction AC Milan vs Benfica
- 5 First, a word on our free tips
- 6 No commitment from us
- 7 Information changes fast
- 8 Your role
- 9 Responsible gambling first
- 10 Legal age
- 11 About the images…
AC Milan vs Benfica : 11 unbeaten for one side, fifth place that cost dearly for the other 
Benfica are still unbeaten this season. Eleven competitive games, nine wins, two draws, and seven straight victories to close out the run.
AC Milan now open their league phase against the most consistent side in the field. Kick-off is set for San Siro on Wednesday 16 September at 21:00 CEST.
The Rossoneri are in the Europa League for one very specific reason. Their poor finish last season left them fifth in Serie A and short of the Champions League places.
Benfica took a much longer road to get here. Third in Portugal behind Sporting and Porto, they had to clear three qualifying rounds this summer.
St Gallen were brushed aside in the second round on a 6-2 aggregate. Hearts followed in the third round (7-2), then Aarhus in the final round (6-2).
That run of high-stakes games has had a clear effect on Benfica’s sharpness. The Portuguese side arrive match-fit, while Milan have played only four league games.
Ruben Amorim has been in charge of the Rossoneri since this summer, after a failed spell at Manchester United. His side have eight points from four Serie A matches, with two wins and two draws.
The last official meeting between these two clubs came in 2007, in the Champions League group stage. It finished 1-1 twice, in the same year Milan won their seventh European crown.
That history only tells you so much. But it does tell you one useful thing: Benfica have never lost to Milan in an official match.
Both clubs have their eyes on the top eight in the league phase, which would mean no February play-off. So this opener carries a bit more weight than your usual warm-up.
AC Milan : back-to-back draws and a Diego Moreira brace to rescue the Olimpico 
Milan started Serie A with two wins, 2-1 in Turin and 2-0 at home to Venice. The streak ended on matchday three.
Juventus held the Rossoneri to a 1-1 draw in their first big test of the season. Last Saturday, the trip to Lazio brought a second straight draw.
That 2-2 at the Olimpico deserves more than a glance at the table. Milan were 2-0 down at the break, punished by Matteo Cancellieri and Tijjani Noslin.
Amorim made three changes at half-time and the game turned. Diego Moreira scored both equaliser, in the 65th and 67th minutes.
The Portuguese winger arrived from Strasbourg in the 2026 summer window and has just delivered his first big display in Rossonero colours. Goncalo Ramos, signed from PSG in the same window, completes a forward line that has been rebuilt from top to bottom.
The comeback also said something less flattering about Milan’s first-half showing. Conceding twice before the interval against a direct rival is hardly a great sign at the back.
In midfield, Adrien Rabiot has one goal and one assist in Serie A this season. Luka Modric is the other reference point in the engine room, but a start on Wednesday is not guaranteed after the Rome trip.
Rotation is the real issue for Milan this week. They are competing on three fronts with a squad that was heavily reshaped over the summer.
Cisse fits that picture with two goals in three league games. Back from a successful loan at Catanzaro, he has made an immediate impact in attack.
The only confirmed absentee is Matteo Gabbia, who has an ankle problem. Everyone else is available, giving Amorim full room to manoeuvre in front of the home crowd.
Try it for $0.99.
Benfica : Pavlidis and Prestianni lead the most productive attack in the field 
Benfica have dropped only one point in the Primeira Liga, a 2-2 draw with Academico de Viseu on the opening day. Everything else has been a win.
Casa Pia shipped seven, Estoril fell 2-1, Maritimo conceded three and Moreirense four. On Sunday, Gil Vicente were beaten 3-1 at the Estadio da Luz.
That latest result showed the Lisbon side’s ability to respond under pressure. Trailing after seven minutes through Hector Hernandez, Benfica did not level until the 29th.
Vangelis Pavlidis scored the first two, including a penalty in the 88th minute. Gianluca Prestianni wrapped it up deep into stoppage time, in the 96th minute.
Those two tell the story better than any league table. Pavlidis has eight league goals, Prestianni six, with both also on the scoresheet in Europe this summer.
This is not a one-man attack. Sharing the load between two forwards makes life much harder for the opposition back line.
At the back, Clement Lenglet has settled in since arriving from Atletico Madrid. Joao Palhinha, signed from Bayern Munich in the 2026 summer window, holds the midfield together.
Norwegian winger Andreas Schjelderup gives them a third attacking option, with one goal and two assists in the league. That gives the club real rotation options despite a busy schedule.
Alexander Bah is missing again, after another physical setback. The Danish full-back played only nine league matches last season for the same reasons.
That is the only confirmed absence for the Portuguese side heading to Lombardy. Benfica arrive at San Siro with most of the main names still in place.
Probable AC Milan team: Not announced at time of publication.
Probable Benfica team: Not announced at time of publication.
Europa League prediction AC Milan vs Benfica
Our prediction: Benfica to avoid defeat at San Siro (draw or Benfica win)
Benfica are on an 11-game unbeaten run and have won seven in a row, including that comeback against Gil Vicente last Sunday. No other side in action on Wednesday can match that level of consistency.
Milan, meanwhile, come in off consecutive draws against Juventus and Lazio, with two goals conceded in the first half at the Olimpico. Pavlidis’ eight league goals and Prestianni’s six should find openings in this defence.
The head-to-head points the same way, with two 1-1 draws in the only official meetings between the clubs in 2007. Back Benfica to stay unbeaten at San Siro, at odds of 1.60.
in your pocket.
Real-time notifications & alerts
_________
First, a word on our free tips
- What we publish on mathodds is analysis, nothing more. We share an opinion, a read on the moment, but never a guarantee. Sport is what it is: unpredictable. A red card, an injury, a freak goal from nowhere… and the whole script changes.
- Let’s be clear: there is no such thing as a risk-free bet. Even when something looks obvious, it never really is. And yes, that means you can lose. That is inevitable sooner or later.
- The smart move is to stay sensible. Bet small, set a budget and stick to it. Do not touch money you need to live on. And above all: do not chase losses, because that rarely ends well.
- A bet should stay a game, not a job or a source of income. If you feel it’s taking up too much of your day, making you angry or putting you under pressure, take a break. And if you need help, speak to a specialist service. That is what it’s there for.
- At the end of the day, the responsibility is yours. Reading our content means accepting that risk exists and will never disappear, even with the best analysis in the world.
- Important reminder: betting is illegal for minors and must comply with the law in your country. Gambling can quickly go off the rails (money loss, family tension, addiction). Need Help? Call 1-800-GAMBLER. In the UK? Visit https://www.gambleaware.org/https://www.gambleaware.org/.
No commitment from us
Our predictions are not a contract. They carry no legal force. In plain English: you cannot use them to demand anything if a bet loses.
Information changes fast
A prediction is always based on what we know at the time of writing. But then a team sheet changes, a player gets injured, the weather turns… and the analysis can be out of date in a flash. We cannot be held responsible for that.
Your role
Before betting, simply check that wagering is legal where you are. If it is not, that is your responsibility, not ours.
Responsible gambling first
We cannot say it often enough: gamble in moderation. If you struggle to stay in control, do not wait to get help. We cannot be responsible for compulsive or excessive use of the information published on the site.
Legal age
mathodds content is for adults only. By browsing here, you confirm that you are old enough to bet under the law.
About the images…
The AC Milan and Benfica images and logos on mathodds, including those linked to the Europa League, are used only to illustrate our articles. They do not mean we have any official link with a federation or sports organisation, and we do not claim any rights over them.
Those rights belong to the original creators. If, despite our care, any visual causes a problem, contact us: it will be removed without delay.
Our only aim in using these images is to make the reading experience better. Nothing more. No commercial gain, no taking credit for someone else’s work.
Leave a Reply