Manchester City was eliminated from the Club World Cup as Al-Hilal pulled off an impressive 4-3 victory in extra time of an intense last-16 match in Orlando.
Markos Leonardo scored his second goal in the 112th minute, leading the Saudi Arabian team to a remarkable upset.
Bernardo Silva gave City an early lead in the ninth minute, but Pep Guardiola's team paid the price for squandering several opportunities as Leonardo and Malcom found the net in the second half.
Erling Haaland equalized to force extra time, and City once again leveled the score through Phil Foden after Kalidou Koulibaly put Al-Hilal in front.
City, who were repeatedly caught on the counterattack, were undone once more by Leonardo, who secured the victory for the Saudi team, setting up a clash against Fluminense for a spot in the semi-finals.
Despite Guardiola taking the competition seriously, he will be disappointed with his team's wasteful performance in the first half.
City started brightly with Ruben Dias heading straight at Yassine Bounou.
Although the opening goal was controversial due to complaints of handball against Rayan Ait-Nouri and Ilkay Gundogan.
Tijjani Reijnders cleverly set up Ait-Nouri, but there were doubts about the ball brushing the Algerian's hand before crossing to Silva.
The referee was unperturbed by Al-Hilal players' protests, and the goal stood.
City missed several chances to extend their lead before the break, with Bounou denying Savinho, Gundogan, Josko Gvardiol, and Jeremy Doku.
Despite City's dominance, Al-Hilal threatened through Leonardo and Malcom.
City's lack of attention to these warnings cost them dearly as Al-Hilal scored two quick goals early in the second half.
City needed to rally, and they did so from a Silva corner that caused chaos in the box.
Haaland capitalized on the opportunity to level the score, but City remained susceptible to Al-Hilal's attacks.
Both teams had opportunities, with City feeling relieved after an offside flag and a crucial tackle by Manuel Akanji prevented further Al-Hilal goals.
City was close to scoring through Akanji and Haaland, but luck was not on their side.
The game headed into extra time after a series of tense moments and attacks from both sides.
City, who had lost Haaland to injury, were shocked when Al-Hilal took the lead again with Koulibaly's header.
However, the drama continued as Foden, who had come on for Rodri, scored a fantastic volley from a Rayan Cherki cross.
Al-Hilal refused to back down and Leonardo found the net once more to secure the victory, despite Ederson's initial save from a header by Sergej Milinkovic-Savic.