Real Madrid suffered a shocking Champions League exit at the hands of their former coach, Jose Mourinho, as his Benfica side advanced thanks to a last-gasp goal from their goalkeeper on Wednesday. Titleholders Paris Saint-Germain also join the Spanish giants in the knockout playoffs.
Madrid, starting the match third in the 36-team standings, fell 4-2 to Benfica despite two goals from Kylian Mbappe, dropping to ninth, just outside the automatic round of 16 spots.
Dramatically, Benfica only secured progression on goal difference, with Ukrainian goalkeeper Anatoliy Trubin scoring a stoppage-time header in the eighth minute after Madrid had been reduced to nine men. Red cards for Raul Asencio and Rodrygo came just minutes earlier, sealing an unforgettable night for the Portuguese side.
"This victory is historic and important," Mourinho said. Speaking about his goalkeeper, he added, "We knew that he could do it. You have to put the ball there, but it is an amazing goal for the guy."
Trubin called it a "crazy moment. I am not used to scoring. I am 24 years old, and it is the first time."
Madrid fell out of the top eight when Sporting Lisbon scored a stoppage-time goal in a 3-2 win at Athletic Bilbao.
"They have outplayed us," Real Madrid coach Alvaro Arbeloa said of Benfica. "We have been far from the version we should be."
Sporting surprisingly joined Liverpool, which beat Qarabag 6-0 with a goal from Mohamed Salah, Tottenham, Barcelona, Chelsea and Manchester City in sealing top-eight finishes. Table-topping Arsenal, which completed a perfect eight-win campaign by beating Kairat Almaty 3-2, and second-place Bayern Munich had already advanced to the round of 16, which begins in March.
Paris Saint-Germain and Newcastle both started in the top eight but drew 1-1 in Paris, sending both down to 11th and 12th in the standings. The game had an explosive start when Newcastle conceded a handball penalty in the first minute, and Ballon d'Or winner Ousmane Dembele saw his spot kick saved by Nick Pope.
Madrid, PSG, Newcastle, and last year's beaten finalist Inter Milan all will be in the qualifying playoff draw Friday for teams that placed ninth through 24th.
Still, PSG went through the playoffs last year, taking the longest path with two extra games in February on the way to its first European title.
"We do not have to think about it too much," said Vitinha, who gave PSG an eighth-minute lead. "We had the same problem last year, and then out of nowhere, things changed, and the ball started to go in."
There is a 50-50 chance it will be Mourinho's Benfica against Real Madrid and Mbappe two more times next month.
The playoff bracket means the ninth-place team, Madrid, can be drawn only against the team that placed either 23rd or 24th, Bodo/Glimt or Benfica.
If Benfica is not paired with Madrid, then it will be the 10th-place team, Inter Milan, whom Mourinho led to the 2010 Champions League title. It is a remarkable renaissance for Mourinho, who lost his job at Fenerbahce in August after a Champions League qualifying playoff defeat.
Norwegian debutant Bodo/Glimt will be a popular addition to the knockout phase, claiming 23rd place by winning 2-1 at Atletico Madrid. That result showed how crucial it was for them to beat Manchester City last week inside their Arctic Circle home.
Benfica's late drama eliminated Marseille, which lost 3-0 at Club Brugge and fell below the cutoff into 25th place with nine points.
Also in the playoffs are Qarabag, Club Brugge, Galatasaray, and Olympiakos, plus Juventus and Atalanta from Italy.
Italian champion Napoli was ousted in 30th place after losing 3-2 at home to Chelsea.
At halftime Wednesday, in-play standings showed Chelsea in 12th and Barcelona 13th, both heading for the playoffs.
Barcelona trailed at home to lowly Copenhagen, whose goal came from 17-year-old Icelandic striker Viktor Dadason, who scored three times in his debut Champions League season.
Barcelona turned the game around in the second half with a 4-1 win, powered by goals from Robert Lewandowski, Lamine Yamal, Raphinha, and Marcus Rashford.