Al Hilal pulled off a sensational win over Manchester City in Florida, securing a 4-3 extra-time victory over the English giants to advance to the quarter-finals of the Fifa Club World Cup.
Marcos Leonardo scored his second goal of the match in the 112th minute after the game ended 2-2 after 90 minutes. Phil Foden's goal in first-half extra time set up a nervy finish, but the Saudi Arabian side held on to claim a famous victory, and with it a place in the last eight where they will face Brazil's Fluminense on Friday.
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.
The decisive goal came after Sergej Milinkovic-Savic's header was well saved by City goalkeeper Ederson, but the ball fell kindly for Leonardo, who slotted into an empty net to spark wild celebrations on the Hilal bench led by new coach Simone Inzaghi.
"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."
Guardiola will rue a wasteful first-half display, while credit must also go to Hilal's Moroccan goalkeeper Yassine "Bono" Bounou, who made 10 saves in all.
City started quickly with Ruben Dias heading straight at Bono. There was a hint of handball in the build-up to City's opener, with Rayan Ait-Nouri and Ilkay Gundogan both given the benefit of the doubt, before Silva prodded home the Algerian's cross.
Al Hilal players surrounded referee Jesus Valenzuela but the Venezuelan was unmoved.
City should have extended their lead before half time but Bono denied Savinho, Gundogan, Josko Gvardiol and Jeremy Doku.
Silva had a shot parried but, after riding their luck, Al Hilal went close through Leonardo and Malcom.
City failed to heed those warnings and were punished as Al Hilal struck twice in the first seven minutes of the second half.
The equaliser came as former City full-back Joao Cancelo drove in a low cross. Ederson pushed away and Malcom’s attempt on the rebound was blocked, but the ball looped up for Leonardo to head in.
City were stung again moments later as Al Hilal quickly recycled the ball from a corner they were defending.
Malcom broke from halfway and buried a low shot into the far corner.
City needed to respond and did so as a Silva corner led to a goalmouth scramble.
Haaland pounced from close range to level but, far from settling nerves, the Premier League side remained vulnerable.
Malcom was brought down by Dias for what seemed a certain penalty only for an offside flag to spare City. It also took a good recovery tackle by Manuel Akanji to prevent Malcom getting in another shot and Mohamed Kanno fluffed a free header.
City were inches away as Akanji headed against the post and Haaland’s follow-up was cleared off the line.
City, who lost Haaland to injury, were stunned when Al Hilal reclaimed the lead with Koulibaly’s powerful header in the first period of extra time.
Yet the drama was far from over as Foden, having come off the bench to replace another substitute in the ineffective Rodri, exquisitely volleyed in from a Rayan Cherki cross.
Al Hilal refused to lie down and scored yet again as Leonardo pounced.
It capped what has been a disappointing year for City, who surrendered their Premier League crown and finished the season without a trophy having also lost the FA Cup final.
But while City's sojourn may be over, Al Hilal's will continue when they return to the same stadium on Friday to play for a place in the Club World Cup semi-finals.
- Steve Luckings
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