Milan have enjoyed a positive start to the season, with Ruben Amorim’s men unbeaten in their last four outings in all competitions, but they faced a tough challenge against a Benfica side that had lost just one of their 12 competitive games (W9, D2) this term.
Here, it was the Eagles who got off to the better start, taking the lead around the quarter-hour mark. Dodi Lukebakio collected the ball on the right flank and dribbled inside before curling a pinpoint shot into the bottom corner.
Buoyed by the opener, Benfica’s momentum grew, and they went close to netting a second when only the woodwork denied Heorhiy Sudakov’s low drive from 25 yards out.
Milan, meanwhile, struggled to gain a foothold in the contest, going into the break knowing they needed to drastically improve.
Recent history, though, suggested they had a good chance of finding the back of the net themselves; seven of their previous 10 games in Europe saw both teams score, while 10 of their last 12 competitive goals had come beyond the hour mark.
Amorim, who played for Benfica as a player, turned to his bench ahead of the restart, introducing Mario Gila and Christian Pulisic. As a result, there was an immediate upturn in Milan’s attacking output, with Koni De Winter firing a glorious opportunity over the crossbar from inside the area.
Nevertheless, Benfica stunted their opponents' attempt to build momentum and doubled their lead in emphatic fashion when Jakub Kaminski powered Souffian El Karouani’s cross into the roof of the net.
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The Rossoneri poured forward in response, throwing caution to the wind as Pulisic was denied by a strong hand from Anatoliy Trubin at his near post.
On the whole, though, Marco Silva’s men produced a solid defensive display, restricting the home side to half-chances on a frustrating night for the home side.
A first competitive defeat will leave Amorim frustrated as he lost to Benfica for just the second time in seven meetings in the dugout. Meanwhile, Silva will be hoping this is a sign of things to come as his side go in search of a maiden Europa League triumph.
Flashscore Man of the Match: Souffian El Karouani (Benfica)