AC Milan and Benfica will renew one of European football's most storied rivalries Wednesday when the former champions meet at San Siro to open their Europa League campaigns.
Both clubs fell short of expectations last season, missing out on Champions League qualification, but each enters the competition among the leading contenders to lift the trophy in Frankfurt next spring.
Milan's failure to secure a place among Europe's elite followed a dramatic collapse at the end of last season. Six defeats in their final 10 Serie A matches cost them valuable ground and ultimately triggered a sweeping change in the club's leadership.
Max Allegri's second spell in charge lasted only a year before he was replaced by Ruben Amorim, who has overseen an unbeaten start to the new campaign.
The Rossoneri opened with wins over Torino and Venezia before drawing their next two league matches. Juventus snatched a late equalizer in Turin, while Milan showed greater resilience against Lazio, recovering from two goals down to earn a point in Rome.
After missing out on European competition altogether last season, Milan are back on the continental stage for the first time since their Champions League knockout-round playoff exit in 2025.
For Amorim, the Europa League also offers a chance to rebuild his European reputation after his Manchester United side lost the 2025 final. The Portuguese previously established himself as one of Europe's most promising coaches during a successful spell at Sporting Lisbon.
That makes Wednesday's meeting particularly intriguing. Amorim spent nine years at Sporting as a player and, as a coach, regularly enjoyed the upper hand over Benfica in Portugal.
History, however, offers the visitors little encouragement.
Benfica have never beaten Milan in six competitive meetings, including European Cup finals in 1963 and 1990. The Portuguese giants will nevertheless arrive in Italy in confident mood after an impressive run of form under new coach Marco Silva.
Benfica also endured a disappointing domestic campaign last season, finishing third in the Primeira Liga under Jose Mourinho. That forced them to navigate the Europa League qualifying rounds, where Silva's tenure began with an unexpected defeat to Swiss side St. Gallen.
The Eagles quickly recovered, crushing St. Gallen 5-0 in the second leg before sweeping aside Hearts 7-2 and AGF 6-2 on aggregate to reach the league phase.
Since then, Benfica have been perfect domestically, winning four straight matches while scoring 12 goals. Their latest victory was particularly dramatic, with a late surge turning a potential draw against Gil Vicente into a 3-1 win and extending their winning streak to seven matches in all competitions.
Silva's side now face a demanding stretch, beginning with Wednesday's trip to Milan before an away meeting with Porto.
Milan could make changes for the midweek fixture, although Amorim is expected to retain his familiar 3-4-2-1 formation.
The hosts appear to have a near-fully fit squad after defenders Mattia Gabbia and Mario Gila recovered from minor problems to make the squad against Lazio.
One of the biggest selection questions surrounds Luka Modric. The 41-year-old midfielder has made 156 appearances in European competition, but his last appearance outside the Champions League came in November 2011.
Amorim also has several options available in the attacking positions behind Goncalo Ramos. Alphadjo Cisse, Alexis Saelemaekers, Ruben Loftus-Cheek, Omari Hutchinson and Christian Pulisic are all competing for places.
Ramos will have an added incentive if selected, with the former Benfica striker facing his old club.
Benfica, meanwhile, will look to Vangelis Pavlidis to provide the attacking threat. The Greek striker scored six goals during qualifying and has already added eight in the Primeira Liga.
Pavlidis has also maintained an impressive scoring rate in UEFA competition, averaging a goal every two matches.
Benfica will be without Alexander Bah, who remains sidelined with a shoulder injury. Daniel Banjaqui or versatile captain Fredrik Aursnes could therefore be asked to fill the right-back position.
