Europa League
2026-09-16 - AC Milan vs Benfica
A Sports Betting Pick by Auls
Football: UEFA Europa League Match Day 1
Wednesday 16th September 2026 - Kick Off 8pm
This game is live on TV
AC Milan
Only Real Madrid can boast they have more European Cup trophies than AC Milan, but the latter have fallen away from the once grand standards they set. Not only did they fail to take part in any UEFA competition last season, but AC Milan were not able to use that to their advantage to earn a return to the Champions League and instead have to settle for competing in the Europa League.
Ruben Amorim is now the fifth new manager for Milan since the 2023/24 season and expectations remain high at the club, despite winning one League title since 2011 and having many more finishes outside of the top four in Italy than inside those positions in that time. A decent start has been made domestically, while AC Milan will enter the Europa League expecting to have a big impact in the competition.
AC Milan are unbeaten in 4 games under the new manager, but had begun the season with consecutive wins and now enter this tie after consecutive draws. A run of 4 home games without a win cost AC Milan a top four place at the end of last season, but the side have won the only game played at the San Siro under Ruben Amorim when seeing off Venezia at the end of August.
Benfica
There are a number of multiple time European Cup Winners that have failed to enter the premier UEFA competition in the 2026/27 season and one of those is Benfica. They are another club that are also under new management this season after appointing Marco Silva, who is also well known to English Premier League fans from his time with Fulham.
Unlike the opponent on Match Day 1 of the Europa League, Benfica were playing in European competition last season and that was in the Champions League where they reached the Knock Out Play Off Round. Jose Mourinho was the manager of the club when they lost to Real Madrid, but Marco Silva has guided Benfica through three Qualifying Rounds to merely enter the Europa League Group Stage and that will have helped him settle the squad.
Benfica were beaten at St Gallen in the Europa League Second Qualifying Round First Leg in Marco Silva's first match in charge, but they are unbeaten in 11 in all competitions since then and have won 7 in a row. The side opened the season without winning either of the first 2 away games played, which were both in the Europa League Qualifying Rounds, but Benfica have since won 4 straight on their travels and scored at least three goals in each victory.
Head to Head
The first meeting between AC Milan and Benfica was in the 1963 European Cup Final and was won by the Italian team against the two time defending Champions.
They next met in the European Cup Final in 1990, which was also won by Milan.
AC Milan have hosted Benfica twice and won both matches with the last of those being played in September 2007.
Prediction
There is no doubting the European pedigree of both AC Milan and Benfica, but they will both be incredibly disappointed that they are meeting in the Europa League rather than the Champions League.
With that being said, both clubs have to believe they can have very strong runs in the competition under new managers and this Match Day 1 fixture will feel like a Champions League tie.
That should help the players with the motivational factor and the fans should produce a vibrant atmosphere in what will feel like an important fixture.
Both Milan and Benfica have begun the season in positive form and that may see the two combine for an entertaining fixture on Wednesday. The new format of the UEFA League Phase does remove some of the early jeopardy when it comes to results and that should free up the players a little more allow the two teams to play with attacking intent.
Benfica have really looked strong going forward, but they are also going to be tested by Milan's attackers and it would be a surprise if both teams are not able to get on the scoreboard.
Settling for a 1-1 draw at this early stage of the League Phase would be a surprise and so backing goals looks the right approach to take from what has been displayed by these teams early in the season.
The Pick :
AC Milan 2-1 Benfica
