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 match 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 ex-Barcelona winger Malcom replied after the break.

Erling Haaland sent the game to extra-time, but City needed another equaliser from Phil Foden after ex-Chelsea defender 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 after the Brazilian side shocked Inter Milan in the last 16.

City’s defeat ended hopes of a potential all-English semi-final meeting against Chelsea, with the Blues taking on Brazilian side Palmeiras in the quarter-finals on Friday in Philadelphia (kick-off on Saturday at 2am UK time).

How City were stunned by Al Hilal

Guardiola, having taken the competition seriously, will rue a wasteful first-half display as his side started quickly with Ruben Dias heading straight at ex-Sevilla goalkeeper Yassine Bounou.

The opening goal soon came, although it proved highly controversial with complaints of handball against Rayan Ait-Nouri and Ilkay Gundogan, before Silva poked past Bounou.

City should have extended their lead before half-time, but Bounou denied Savinho, Gundogan, Josko Gvardiol and Jeremy Doku.

City were then punished for their profligacy 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, City goalkeeper 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 before Malcom broke from halfway and buried a low shot into the far corner in the 52nd minute.

But City equalised just three minutes later as Silva’s corner led to a goalmouth scramble and 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 from 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 as the game headed to extra-time.

City, who lost Haaland to injury, were stunned when Al Hilal reclaimed the lead with Koulibaly’s powerful header.

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 to settle the contest after Ederson had pushed away a header from Sergej Milinkovic-Savic.

Guardiola: We were so open in defeat

Man City boss Pep Guardiola said:

“It is a pity. We have been on an 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.

“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 – we did but could not finish it.

“I had a feeling we could go through but they punished us on the transitions.”

Inzaghi: We climbed Mount Everest

Al Hilal head 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.”

Sky Sports to show 215 live PL games from next season

From next season, Sky Sports’ Premier League coverage will increase from 128 matches to at least 215 games exclusively live.

And 80 per cent of all televised Premier League games next season are on Sky Sports.