Manchester City have 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 massive upset and made a statement.
Bernardo Silva gave City a ninth-minute lead but Pep Guardiola's men 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 Brazilian side Fluminense for a place in the semi-finals.
"We knew it was a difficult game against one of the best teams in the world," said ex-Chelsea star Kalidou Koulibaly. "We wanted to show our ideas, our talent, our power and I think that we made a very good game.
Al Hilal coach Simone Inzaghi was delighted.
"We defeated a very, very strong team. That looked impossible yesterday."
Guardiola, having taken the competition seriously, will rue a wasteful first-half display.
"It is a pity. We have been on an incredible journey together and were in a good place. The vibe was really good," he said.
"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."
Earlier, Fluminense stunned Champions League finalists Inter Milan by knocking them out with a 2-0 victory in Charlotte.
The reign of new Inter Milan coach Cristian Chivu, who took over following 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.
Fluminense struck after three minutes when Cano pounced on a deflected cross and headed in from close range, putting the ball in between goalkeeper Yann Sommer's legs for a dream start.
The Italians pushed for an equaliser after the break but were frustrated by a well-organised defence. Stefan de Vrij missed a close-range chance, keeper Fabio denied Sebastiano Esposito with his feet and Lautaro Martinez struck the post.
Substitute Hercules sealed the win for Fluminense three minutes into added time, calmly slotting home from the edge of the box to send the Brazilians through to a last-eight clash with Al Hilal on Friday in Orlando.
Fluminense became the second Brazilian club team to reach the quarter-finals, joining Palmeiras.
Milan certainly had their chances, but couldn't will the ball into the net.
Martinez criticised his teammates publicly after the loss.
"Whoever wants to stay, stay; whoever does not want to stay should go," Martínez told DAZN. "I have seen a lot of things that I didn't like. I want to win."
The forward's comments came after an 11 month-long season where they ended runners-up in both the Champions League and Serie A.