Manchester City crashed out of the Club World Cup as Al-Hilal snatched a stunning 4-3 victory in extra time of a pulsating last-16 clash in Orlando.
Marcos Leonardo grabbed his second goal with 112 minutes on the clock as the Saudi Arabian side produced a major upset.
Bernardo Silva gave City a ninth-minute lead but Pep Guardiola's side were punished for missing a series of chances as Leonardo and Malcom replied after the break.
Erling Haaland sent the game to extra time but City needed another equaliser from Phil Foden after Kalidou Koulibaly headed Al-Hilal back ahead.
City, who were caught repeatedly on the break, were undone again as Leonardo had the final say and the Saudi side will now play Fluminense for a place in the semi-finals.
Man City manager Pep Guardiola immediately turned his thoughts to next season.
He said: "It is a pity. We have been on incredible journey together and were in a good place. The vibe was really good.
"I cannot thank the players enough for training and playing how they have been.
"But it was a difficult game. The margins were minimal. We created a lot and (Yassine) Bounou made incredible saves but we were so open.
"We would have loved to have continued, it will only be once every four years, and we had a feeling that the team was doing well.
"But we go home and now it is time to rest and rest our minds for the new season."
City had been strong favourites to prevail and go through to a quarter-final clash against Fluminense, the side they thrashed 4-0 in the 2023 final, but Guardiola conceded there were shortcomings at both ends of the field.
He said: "We regret a little bit that we allowed them to run a bit more. They defended so deep, the wingers were so quick and Bounou made a lot of saves.
"In the end, we have to score and be clinical. They arrived more in the transitions. They did not create much in the first half but we did but could not finish it.
"I had a feeling we could go through but they punished us on the transitions."
The result underlines the rapid of acceleration of Saudi football in recent years.
Al-Hilal coach Simone Inzaghi said: "The key to this result was the players, the heart they put on the pitch.
"We had to do something extraordinary because we knew how good Manchester City are, we knew we had to climb Mount Everest without oxygen and we were great.
"Guardiola is the best coach in the world but tonight we did our best and we deserved the result."
Brazilian side Fluminense stunned Champions League finalists Inter Milan by knocking them out of the Club World Cup with a 2-0 victory in Charlotte.
The reign of new head coach Cristian Chivu, who took over following Simone Inzaghi's departure just days after that humbling loss to Paris St Germain a month ago, has not started well as they exited the tournament before the quarter-finals.
Goals from German Cano, after just three minutes, and Hercules in the third added minute at the end of the game sealed the Serie A side’s fate.
Fluminense will take on Al-Hillal in the quarter-finals.
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