AC Milan's journey in the UEFA Champions League came to an end as they were held to a draw by Feyenoord in the second leg of their knockout play-off at San Siro Stadium.
The Italians quickly erased a 1-0 deficit from the first leg, with Santiago Gimenez scoring just 36 seconds into the match, marking the fastest goal of this season's Champions League.
However, the situation turned for Milan when full-back Theo Hernandez received a red card in the 51st minute after accumulating two yellow cards. Feyenoord's Julian Carranza then scored the crucial goal in the 73rd minute, securing a 2-1 aggregate victory, as reported by BBC Sports.
The draw for the last 16, scheduled for Friday, will determine whether Feyenoord will face Inter Milan or Arsenal next month.
Milan, who have won the European title seven times, started strong with Gimenez's early goal. Christian Pulisic delivered a cross to the back post, which Malick Thiaw headed back into the box, allowing the Mexico international to score from close range—his sixth goal in the competition, five of which were scored while he was with Feyenoord before his winter transfer.
Feyenoord sought to take the aggregate lead, with Tijjani Reijnders and Joao Felix coming close to scoring, while Hernandez's powerful shot hit the post in the 23rd minute.
In the closing moments of the first half, Rafael Leao was thwarted by Feyenoord goalkeeper Timon Wellenreuther, who also saved a low drive from Kyle Walker early in the second half.
The Dutch team, managed on an interim basis by Pascal Bosschaart, received a significant advantage when French player Hernandez was shown a second yellow card for simulation just six minutes into the second half.
Feyenoord took full advantage of the extra player, with Carranza connecting with a cross from Hugo Bueno to deliver a powerful header past Milan's captain, Mike Maignan, securing their place in the last 16 of the prestigious European tournament for the first time since 1974.
Unfortunately, they will be without Givairo Read for the upcoming last-16 match, as the right-back was issued a red card for violent conduct following a heated exchange between the teams after the final whistle.
