Real Madrid were dramatically pushed into the Champions League qualifying play-off round after a chaotic defeat by Benfica.
The Spanish giants began the night sitting third in the 36-team league standings. Despite two goals from Kylian Mbappé, they slumped to a 4-2 loss in Lisbon.
The result saw Madrid fall to ninth place, one position outside the automatic qualification spots for the last 16.
Former Madrid manager José Mourinho masterminded the upset as Benfica scraped into the knockout phase in 24th place. They progressed only on goal difference.
The decisive moment came deep into stoppage time. Goalkeeper Anatoliy Trubin surged forward and headed in a dramatic 98th-minute goal.
Madrid were already in trouble by then. Two red cards had reduced Álvaro Arbeloa’s side to nine players late in the match.
Benfica’s late goal coincided with decisive results elsewhere. Sporting Lisbon’s stoppage-time winner against Athletic Bilbao pushed Madrid further down the table.
Sporting secured a top-eight finish alongside Liverpool, Tottenham, Barcelona, Chelsea and Manchester City. Arsenal and Bayern Munich had already confirmed their places earlier.

Paris Saint-Germain also suffered a damaging night. A 1-1 draw with Newcastle United in Paris caused both sides to slide out of the top eight.
PSG dropped to 11th, with Newcastle ending the league phase in 12th position.
Madrid, PSG, Newcastle and last season’s runners-up Inter Milan will now contest the play-off round. The draw for teams placed ninth to 24th will be held on Friday.
The play-offs will add two extra matches to already crowded schedules. It marks a rare setback for Madrid, who are accustomed to direct qualification.
For Benfica, the night delivered both survival and drama. Mourinho’s side advanced in the most unlikely fashion, leaving European heavyweights to fight for their place.
The Champions League last-16 picture is now set for a tense and unpredictable next phase.
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