Marcos Leonardo scored his second goal of the match in the 112th minute to give Al Hilal a 4-3 upset victory over Manchester City on Monday night in Orlando, sending the Saudi Arabian side into the quarterfinals of the Club World Cup.
Malcom and Kalidou Koulibaly also scored for Al Hilal, who got 10 saves from goalkeeper Yassine Bounou.
Al Halil will meet Fluminense on Friday at Orlando. The Brazilian side beat Inter Milan 2-0 earlier Monday.
Bernardo Silva, Erling Haaland and Phil Foden were the goal-scorers for Manchester City.
The decisive goal came after Sergej Milinkovic's header was stopped by Ederson for the Manchester City goalie's second and final save of the match.
The ball then hit off Leonardo to the left front of the goal line, and he knocked the ball into the open net with his right foot to give Al Hilal the lead.
Koulibaly scored on a header to give Al Hilal a 3-2 lead in the fourth minute of extra time.
Al Hilal's Ruben Neves took a corner kick, and Koulibaly leaped and flicked the ball to the left of Ederson.
Manchester City had two strong chances late in the second half of regulation time.
Off a corner kick in the 84th minute, Manuel Akanji sent a header that hit off the right goalpost. Haaland was there for a potential tap-in, but Al Hilal's Ali Lajami cleared the ball before it crossed the line.
One minute later, Ruben Dias delivered a hard fight-footed blast from outside the box that Bounou knocked over the crossbar with his right hand.
Al Hilal received goals from Leonardo and Malcom in the first seven minutes of the second half to turn a one-goal halftime deficit into a 2-1 lead.
It took just 42 seconds into the half for Al Hilal to get the equalizer.
City goalkeeper Ederson stopped a left-footed shot from Nasser Al Dawsari, and a rebound attempt by Malcom was blocked by a defender. The ball went directly to Leonardo, who easily headed it into the net.
Al Hilal moved ahead in the 52nd minute on a breakaway. Former City player Joao Cancelo cleared the ball ahead from deep in his own end up to Malcom, who dribbled in and drilled a left-footed shot past Ederson and inside the far post to give Al Hilal a 2-1 lead.
Just three minutes later, Manchester City tied the match off a corner kick. Haaland attempted a header that barely glanced off him, but the ensuing scramble led to the ball coming back his way, and Haaland sent a left-footed shot through Bounou's legs.
Manchester City dominated the first half and had a 7-0 edge in shots on target while holding the 1-0 halftime lead.
Silva's goal in the ninth minute was controversial as the ball hit off the right biceps of teammate Rayan Ait-Nouri. An ensuing pass saw the ball deflected, and it caromed in the direction of Silva, who sent a left-footed shot into the left corner of the net.
Al Hilal players vehemently argued to no avail as the goal stood up.
Bounou repeatedly made big saves to keep Al Hilal in the game. He was sprawled on the ground when he made a save with his left hand on Savinho in the 24th minute, and he thwarted Josko Gvardiol's header six minutes later.
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