AC Milan vs Benfica Preview: Amorim’s European Return Against the Club He Played For, and a Record Stretching Back to 1963

Two of the most decorated clubs in European football meet in UEFA’s second competition tonight, and the storyline writes itself: Ruben Amorim spent nine years at Benfica as a player, and his first continental match as AC Milan head coach comes against them. Milan are unbeaten under him but have drawn their last two. Benfica arrive on a seven-match winning run with 21 league goals already on the board. And hanging over all of it is a head-to-head record that says Benfica have never beaten Milan in six major European meetings — two of them European Cup finals.

Two Former Champions, One Tier Down

That both of these sides are here at all is the story of the summer. Milan finished outside the Champions League places last season, which cost Max Allegri his second spell in charge after a single year and brought in Amorim. It is his first European campaign with the club, and Milan’s first in this competition since 2020/21 — their most recent continental football of any kind came in the 2024-25 Champions League, where they went out in the knockout-round playoffs.

The start has been solid rather than spectacular. Wins over Torino and Venezia were followed by a late Juventus equaliser in Turin and then a comeback from two goals down in Rome to draw 2-2 with Lazio, a match in which the substitutes — Diego Moreira especially — changed the game. Eight points from four matches leaves them fifth. Amorim has used a different eleven in each outing so far, and his pre-match press conference suggested he has now settled on the version of the team he wants.

Benfica’s route here was more dramatic. They finished third in Portugal last season under Jose Mourinho, which meant a qualifying path for new coach Marco Silva, appointed from Fulham. That path began with a shock 2-1 defeat at St. Gallen before a 5-0 second leg turned it around, and continued with 7-2 aggregate wins over Hearts and Aarhus. Since a 2-2 draw with Academico de Viseu on the opening league weekend they have won every match: 7-0 against Casa Pia, 2-1 against Estoril, 3-0 at Maritimo, 4-0 at Moreirense and 3-1 against Gil Vicente. Twenty-one goals scored, four conceded, and a trip to Porto waiting at the weekend.

Head-to-Head: Six Meetings, Two Finals, No Benfica Win

These are not teams who meet often — but when they have, it has tended to matter. The first two encounters were European Cup finals. In 1963 at Wembley, Jose Altafini scored twice after Eusebio’s opener as Milan came from behind to win 2-1 and lift the trophy for the first time. In 1990 in Vienna, Frank Rijkaard got the only goal. In between and since, Milan have never lost: a 2-0 win at San Siro and a goalless second leg in the 1994-95 Champions League quarter-finals, then 2-1 at home and 1-1 away in the 2007-08 group stage.

Four Milan wins, two draws, no Benfica victory in six major European meetings. The clubs also met once in the 1955/56 Latin Cup semi-final, a 4-2 Milan win, which sits outside the UEFA record. The most recent meeting of any kind was the 1-1 draw in Lisbon in November 2007.

Four Things to Watch

1. Amorim against the club he played for

He spent nine years at Benfica as a player and, as Sporting coach, lost only one of his last six meetings with them. He also took Manchester United to the Europa League final in 2024-25, losing 1-0 to Tottenham. So this is a return to a competition he knows the far end of, against opponents he knows better than most. The emotional thread is obvious; the practical one is that he has had four games to work out what this Milan side actually is.

2. Gonçalo Ramos against his old club

Milan’s centre-forward came through at Benfica, and so did Diego Moreira, who scored twice off the bench against Lazio. Both are expected to be involved tonight. Ramos is the focal point of Amorim’s attack in a 3-4-2-1, and with Pulisic and Cisse either side of him this is the most attacking shape Milan have fielded all season.

3. Pavlidis is in the form of his life

The Greek striker scored six times in qualifying and already has eight in the Primeira Liga this season, and his record in UEFA competition is a goal every two games. He is the single most in-form player on the pitch. Behind him, the 20-year-old Prestianni has ten goal contributions in ten matches, Rafa Silva and Schjelderup provide the width, and Joao Palhinha — rested at the weekend — returns in the holding role.

4. Modric’s first Europa League night in fifteen years

The 41-year-old has made 156 major European appearances, but only 14 of them outside the Champions League, and his last in this competition was in November 2011 — scoring for Tottenham in a defeat to PAOK. Whether he starts or comes off the bench, it is a striking measure of how far Milan have travelled to be here.

Predicted Lineups

Neither side had confirmed a starting eleven at the time of writing. The selections below follow projected line-ups published by SempreMilan, Sports Mole and Khel Now, cross-checked against the sides that started against Lazio and Gil Vicente respectively. The one recurring difference of opinion is in Milan’s midfield and wing-back slots, so treat those as provisional.

Key Battle: Pavlidis Against Milan’s Back Three

Benfica will play 4-2-3-1 with the ball and ask Pavlidis to run the channels, with Prestianni drifting inside from the right and Schjelderup attacking the left. Milan will defend in a back three of Gila, De Winter and Pavlovic, with wing-backs Chukwueze and Moreira asked to push high when possession turns over. That structure has a known weak spot: the Rossoneri have conceded in each of their last two league matches, and three goals across those games came from situations where the back line was dragged wide.

Which makes the midfield screen the real hinge. Rabiot and Musah have to stop Palhinha and Barreiro from feeding Pavlidis early, because if Benfica’s striker receives the ball facing goal he has scored at a rate of one every two UEFA appearances this calendar year. If Milan can force Benfica wide and make Soares play long, the home crowd gets a foothold; if they cannot, this becomes a very open European night very quickly.

Kit Note: Rossoneri Red and Black, Eagles Red and White

Milan’s 2026/27 range is one of the deepest in the shop: home, away and third shirts for the current campaign, plus the home shirt in long-sleeve, kids and womens cuts. Benfica are thinner on the ground but their current home and away are both in stock, and for the heritage angle there is a Milan home shirt from the 1993/94 season — the era either side of that 1995 quarter-final against this same opponent. Here is what is available.

AC Milan — home, away, third, long sleeve, kids and womens

Swipe to browse 6 AC Milan shirts

AC Milan 26/27 Home Shirt

$38.90

AC Milan 26/27 Away Shirt

$38.90

AC Milan 26/27 Third Shirt

$38.90

Milan Home Shirt 2026/27 Long Sleeves

$42.80

Milan Home Shirt 2026/27 Kids

$35.99

Milan Home Shirt 2026/27 Women

$35.99

Benfica matchday, plus a Rossoneri classic from the early nineties

Swipe to browse 2 Benfica shirts and 1 retro Milan

Benfica 26/27 Home Shirt

$38.90

Benfica 26/27 Away Shirt

$38.90

AC Milan Retro Vintage Home Jersey 1993-1994 Men | Foot Sport

$41.90

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