Saudi Arabia's Al-Hilal stunned Manchester City 4-3 in extra-time in Orlando on Monday to pull off one of the shocks of the Club World Cup and set up a quarterfinal against Brazil's Fluminense.
Marcos Leonardo scored his second of the night in the 112th minute as Simone Inzaghi's side saw off the Premier League club, who had taken a ninth minute lead through Bernardo Silva.
Quick-fire goals from Leonardo and Malcom in six minutes immediately after the restart put Al-Hilal in front before Erling Haaland equalised for City in the 55th minute.
Four minutes into extra-time, Kalidou Koulibaly headed in Ruben Neves' corner to put the Riyadh-based club back in front and while Phil Foden levelled again for City Leonardo netted with seven minutes left to take Al-Hilal through.
"We knew it was a difficult game against one of the best teams in the world," said Koulibaly. "We wanted to show our ideas, our talent, our power and I think that we made a very good game.
"Defensively we were very strong and offensively all of the opportunities we could put inside we put in, so we can be happy."
A remarkable victory in extra-time for Al Hilal. ✨#FIFACWC
— Fifa Club World Cup (@FIFACWC) July 1, 2025
Portuguese playmaker Silva had put City ahead when he pushed the ball over the line after Renan Lodi's attempted clearance ended up at his feet inside the six-yard box.
Replays showed the ball had brushed the wrist of City's Rayan Ait-Nouri earlier in the move but the referee waved away the Al-Hilal protests.
Al-Hilal goalkeeper Yassine Bounou then made a string of saves to deny City a second before the interval and within seconds of the restart the Saudi club levelled.
Malcom drove down the right and found Joao Cancelo, whose ball into the six-yard box was initially blocked by a sprawling Ederson but Leonardo headed the looping rebound into the unguarded net.
Six minutes later Malcom was released behind the defence by Cancelo's pass from deep inside his own half and the Brazilian showed composure to stroke his shot past Ederson.
The lead was to last only three minutes, however, as Haaland pounced on Silva's corner and the Norwegian was denied a late winner by a desperate clearance on the line from Ali Lajami.
The Saudis went ahead four minutes into extra-time when Koulibaly rose to glance home a header from a corner but City levelled once again, substitutes Rayan Cherki and Foden combining for the England international to steer a sublime first-time volley across Bounou and into the bottom corner.
Al-Hilal would not be denied and Leonardo claimed his second of the night after seeing Ederson save Sergej Milinkovic-Savic's header, the weary Brazilian stumbling as he steered the winner home.