Milan welcome Benfica while Rúben Amorim chases European classic redemption
The floodlights blaze over the San Siro on Wednesday as Milan host Benfica in what will be the eighth official clash between the Associazione Calcio and the Portuguese giants, a meeting that traces its roots back to the 1950s Taça Latina and two Champions finals.
A historic European rivalry
The confrontation in Milão marks the eighth official meeting between Milan and Benfica, a rivalry that began in the 1950s within the context of the Taça Latina and has grown to include two Champions finals, cementing its status as a European classic. Benfica have only managed to win when the fixture was a friendly, doing so three times.
Rúben Amorim follows a personal trend, having lost just four of his thirteen encounters as a manager against the Águias, and only one of those defeats came on Milan’s home ground. His record therefore stands as a rare bright spot for the Portuguese side.
These figures give weight to what is at stake this Wednesday at the San Siro, the headline match of the first Europa League round. It offers both clubs a chance to build momentum and deepens the evolving relationship between Benfica and Amorim, a bond that the future promises to test further.
Amorim’s lifelong bond with Benfica
Rúben arrived at Benfica in 1994, aged nine, and entered the club’s youth schools, situated between the generation of João Pereira and that of Manuel Fernandes, Miguel Veloso, Fernando Alexandre and João Vilela. He later became a national champion and represented the Lisbon selection alongside Cristiano Ronaldo.
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He left the academy when Vale and Azevedo introduced drastic budget cuts that crippled the youth structure, an episode Pedro Russiano recalled in 2024, saying: “Chorámos muito … não só destruiu as escolas do Benfica como a ligação entre nós.” The cuts put dozens of youngsters on the street, a fact que still haunts the club.
In 2008 Benfica re‑signed Rúben for €1 million, making him a starter at Belenenses, a Cup finalist and UEFA Cup participant. Sporting director Rui Costa praised him, and his membership card bore the number 18 301. Amorim himself had been a member for 23 years, essentially since birth.
Amorim later told Expresso in 2017 that he signed for Benfica “with the heart”, after being promised values in Germany that never materialised. He joined when the club had just finished fourth and endured three coaches in a single season, a turbulent period he later helped to stabilise.
Current stakes at the San Siro
Reflecting on his first year, Amorim explained: “In the first year of Benfica, he wanted to give you a lot of information … he exhausts players, and every two years he has to clean the squad. Many are sold, because he helps many players, but also harms others.” This philosophy will be tested against Milan’s disciplined setup.
The squad that eventually won the national title has brought fierce competition for Amorim, with the arrivals of Ramires and Javi García to form a new diamond midfield. Their presence adds another layer of intrigue to a match that could shape the trajectory of both clubs in the Europa League.