Milan’s underwhelming form this season (W4, D2, L4) was evident early on, as the hosts found themselves under immediate pressure from Club Brugge.
The Blauw-Zwart carved out multiple chances, with Mike Maignan called into action more than once, but it was Joel Ordonez who came closest to breaking the deadlock, rattling the crossbar with a thunderous strike inside the opening 10 minutes.
A resurgent Rossoneri then turned the game on its head after the half-hour mark, as Christian Pulisic’s deceptive corner delivery caught the opposition off-guard and sailed into the net.
Moments later, referee Felix Zwayer issued a straight red card to Raphael Onyedika for a cynical boots-up challenge on Tijjani Reijnders, leaving Brugge with a mountain to climb heading into the second period.
But despite being reduced to ten men, Nicky Hayen's side defied expectations after the break, equalising just six minutes into the second half, when Kyriani Sabbe slotted a composed finish into the bottom corner after a well-timed pass from Christos Tzolis inside the area.
That leveller stunned the San Siro crowd, but the visitors’ joy was short-lived, with Paulo Fonseca’s decision to introduce Noah Okafor on the hour mark immediately paying dividends.
The Swiss international zoomed through the left flank before feeding Reijnders for a first-time finish from point-blank range, as the Rossoneri regained their lead.
And Reijnders, who was clearly eager to atone for last weekend’s red card against Udinese, soon doubled his tally and Millan’s lead with a slick low finish, having received Samuel Chukwueze’s pass from the right.
The Dutchman’s second-half brace was all the Rossoneri needed to secure victory and kickstart what they hope will be a successful continental campaign after what will be an 18-year wait to lift club football’s greatest prize of all, having lost each of their opening two UCL games of the season.
On the other hand, the Blauw-Zwart taste their first away defeat in Europe’s top-tier competition in five outings, while also failing to keep a clean sheet against AC Milan for the first time in three visits to the historic stadium.
Flashscore Man of the Match: Tijjani Reijnders (AC Milan)