Goalkeeper Anatoliy Trubin scored a stunning 98th-minute goal to send Jose Mourinho’s Benfica into the Champions League play-offs after beating Real Madrid.
The Spanish giants also face the play-offs, and could face Benfica again, after dropping from third to ninth with defeat at Estadio da Luz.
Benfica looked set to go out in agonising fashion, on goals scored, despite leading 3-2 with seconds remaining.
However, a free-kick gave them one last chance. Trubin was sent up and the Ukrainian timed his run to perfection to meet the cross with a bullet header past opposite number Thibaut Courtois to spark wild celebrations in Lisbon.
Victory is Mourinho’s first over his former side and sees Benfica reach the knockout stages despite losing their first four games in the league phase.
Mourinho’s men were much the better team for long spells and had missed a number of opportunities and seen a penalty overturned by the video assistant referee before falling behind to a Kylian Mbappe header.
But the hosts were level six minutes later as Vangelis Pavlidis made the most of a slip from Raul Asencio to cross for Andreas Schjelderup, who headed home.
Benfica were cutting through Madrid at will and went in front on the stroke of half-time, Pavlidis scoring from the spot after Nicolas Otamendi went down under a challenge from Aurelien Tchouameni.
It got better for the Portuguese side after the break as Schjelderup was given far too much time and space inside the visitors’ penalty area and fired a shot past Courtois at his near post.
Mbappe pulled one back for Alvaro Arbeloa’s side moments later with a smart finish for his 13th Champions League goal of the campaign to set up a dramatic finale.
There were chances at both ends before Asencio was sent off for a second bookable offence in the 92nd minute. Substitute Rodrygo then earned himself two yellow cards for dissent in the space of a few seconds as Madrid were reduced to nine.
But the drama was not finished with Benfica going on to score the crucial goal in the most remarkable of circumstances.
With Madrid finishing ninth and Benfica in 24th, there is now a 50-50 chance that they will meet again in the play-off round.
