Marcos Leonardo scored a dramatic extra-time winner in the 112th minute to hand Al Hilal a stunning 4-3 victory over Manchester City on Monday night, knocking the English champions out of the Club World Cup in a round of 16 thriller.

Leonardo netted his second goal of the match after pouncing on a rebound from close range. Manchester City goalkeeper Ederson had just saved a powerful header from Sergej Milinkovic-Savic, but the ball landed at Leonardo’s feet.

As he fell near the left post, the Brazilian forward guided the ball in with his right foot, sending the Saudi Arabian side into the quarterfinals.

In a match full of twists and momentum swings at Camping World Stadium, Al Hilal took the lead three times — including twice in extra time — and held on. Kalidou Koulibaly fired them ahead 3-2 in the 94th minute, only for substitute Phil Foden to draw City level in the 104th.

Leonardo had earlier cancelled out Bernardo Silva’s ninth-minute opener with a clinical finish in the 46th minute. Malcom gave Al Hilal a 2-1 lead in the 52nd minute, before Erling Haaland made it 2-2 just three minutes later.

The game saw late drama in regulation as City nearly clinched a winner on a last-gasp counterattack, only to be denied by a heavy challenge inside the box.

Referee César Ramos waved play on, and Manchester City manager Pep Guardiola stormed onto the pitch after the final whistle to protest the decision, though no penalty was awarded.

Al Hilal now advances to face Fluminense of Italy on 4 July at the same venue for a place in the semi-finals. Fluminense booked their quarter-final spot earlier in the day with a win over Inter Milan.

“We defeated a very, very strong team. That looked impossible yesterday,” said Al Hilal coach Simone Inzaghi after the final whistle.

Guardiola, visibly disappointed, said, “It’s a pity… Nothing to say. We’ll have to continue. I still have the feeling this team is doing well. We’ll go home and have time to rest.”