AC Milan were to left rue Theo Hernandez's second yellow card - for diving - as Feyenoord advanced to the Champions League last 16 at the former European champion's expense with a 1-1 draw in the second leg of their playoff.
Bayern Munich, Club Brugge and Benfica also won their playoffs on Tuesday, eliminating Celtic, Europa League winner Atalanta, and French team Monaco, respectively.
"In soccer everything changes in a second," said Milan forward Santiago Giménez, who scored one of the competition's fastest goals against his former team, Feyenoord, in the first minute.
Hernandez was sent off for a dive in the 51st when Milan were dominating after Giménez's opener had leveled the tie. Feyenoord had won the first leg of the playoff 1-0 last week.
But Milan's defence looked anything but assured after referee Szymon Marciniak showed Hernandez another yellow card for his dive. The France defender had earned his first before the break for lashing out at a Feyenoord player after a foul on teammate João Félix.
Hugo Bueno crossed for Julián Carranza to head Feyenoord level on the night in the 73rd, giving the Dutch team a 2-1 win on aggregate.
"We're very disappointed. We started well and scored straight away. It seemed like Feyenoord couldn't hurt us," Giménez said of the game's pivotal moment.
"Today it happened to Theo but it can happen to anyone, this is soccer. We have the utmost respect for Theo. We will give him all our support."
Feyenoord's Givairo Read was shown a red card following another melee after the final whistle.
Feyenoord will play either Inter Milan or Arsenal in the round of 16.
Alphonso Davies scored in the fourth minute of stoppage time for Bayern Munich to reach the last 16 with a 1-1 draw against Celtic in the second half of their playoff.
Davies bundled the ball over the line after Leon Goretzka's effort was kept out, saving Bayern the ordeal of extra time after German player Nicolas Kühn had scored against his former club to draw Celtic level on aggregate.
Davies' goal gave Bayern a 3-2 win over two legs.
Club Brugge eliminated Atalanta with a 3-1 win in Bergamo for a 5-2 win on aggregate. Nineteen-year-old forward Chemsdine Talbi scored twice as the visitors gave Gian Piero Gasperini's team a lesson in efficiency.
Benfica reached the last 16 with a 3-3 draw against Monaco in Lisbon, giving the Portuguese team a 4-3 win on aggregate.
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