quarterfinals

Saudi Arabia’s Al Hilal have sent English giants Manchester City crashing out of the Club World Cup, snatching a shock 4-3 victory in extra time in the biggest upset of the tournament so far.

The match finished 2-2 at full-time on Monday, but at the end of an eventful extra-time, Marcos Leonardo grabbed the winner and pulled off one of the greatest wins in Middle Eastern football history.

The Saudi club now advance to the quarterfinals, where they will face Brazilian club Fluminense, ensuring a non-European team will reach the last four.

Man City had taken the lead in the ninth minute in controversial fashion, with Bernardo Silva finishing after Rayan Ait-Nouri’s cross.

Al Hilal players protested that Ait-Nouri had controlled with his arm in the build-up, but the goal stood.

Man City had plenty of opportunities to extend their lead before the break, but a combination of poor finishing and inspired goalkeeping from Moroccan goalkeeper Yassine Bounou kept the lead at a single goal.

Al Hilal offered several reminders of their threat on the break but Man City had even more chances, with Jeremy Doku volleying straight at Bounou, who moments later reacted superbly again to keep out a Bernardo effort.

The question as to whether Man City would live to regret not converting those chances was answered within a minute of the resumption.

Former City full-back Joao Cancelo’s low cross was parried out by Ederson. Malcolm pounced but saw his shot blocked by Ruben Dias, only for the ball to loop to Marcos Leonardo to head home the equaliser.

Six minutes later, and City’s high defensive line was exposed by a long ball from Cancelo, which Brazilian Malcolm raced onto, showing power and pace as he broke away before coolly slotting past Ederson.

The Saudi fans in the crowd went wild while City manager Pep Guardiola responded immediately with a triple substitution, with midfielder Rodri and defenders Nathan Ake and Manuel Akanji introduced.

That brought some much-needed stability to a shaky back line but City needed improvement at the other end too, and it came, albeit in scruffy circumstances.

The Al Hilal defence were unable to deal with a Bernardo corner and Haaland pounced to steer home the loose ball and make it 2-2.

City piled on the pressure as they looked for the winner but yet again Bounou proved their nemesis as he denied Akanji and Ruben Dias, and even when he was beaten by Haaland, substitute Ali Lajami produced a magnificent goal-line clearance.

Guardiola took off Haaland and introduced Egyptian forward Omar Marmoush as the game went into extra time.

But for all City’s depth, Al Hilal had a deep well of spirit to draw upon. Just four minutes into the opening period, Al Hilal regained the lead when Kalidou Koulibaly rose superbly to meet a Ruben Neves corner with a brilliantly angled header.

City responded with a goal of real quality when Rayan Cherki’s brilliantly floated ball towards the back post was poked home masterfully by Phil Foden, at full stretch and from the tightest of angles.

But incredibly, Al Hilal responded again to restore their lead: Sergej Milinkovic-Savic’s header was saved by Ederson but Marcos Leonardo followed in to bundle the ball over the line.

As the celebrating Al Hilal fans poured out of the stadium, the Brazilian striker let his emotions pour out, too.

“I’ve had a difficult time in the last two months. My mother spent 70 days in the ICU,” he said.

“Today, she’s fine, thank God. When I scored those two goals, I thought of her. She was able to watch the match.”

City skipper Bernardo Silva said his team had paid the price for being unable to deal with Al Hilal’s counter-attacking.

“We scored three and could’ve scored five, six. It was all about controlling when we lost the ball, controlling the transitions, don’t let them run, and they ran way too many times,” he said.

“With one, two passes, there was always a feeling of danger coming from them. When we allow teams to run like this, we always suffer a lot, and today was the case,” he said.

The Brazilian side advance to face either Manchester City or Al Hilal in a quarterfinal on Friday.

Fluminense have reached the Club World Cup quarterfinals with a stunning 2–0 win over Inter Milan as German Cano’s early goal and Hercules’s stoppage-time strike toppled the Champions League runners-up.

Fluminense struck after three minutes when Cano pounced on a deflected cross and headed in from close range, putting the ball through goalkeeper Yann Sommer’s legs for a dream start in the sweltering heat in Charlotte, North Carolina, the US on Monday.

The Brazilian side nearly doubled the lead in the 30th minute, when Sommer spilled Jhon Arias’s initial effort and Samuel Xavier fired the rebound attempt narrowly wide of the far-left post.

And in the 39th minute, Ignacio thought he had doubled Flu’s advantage, only to be ruled fractionally offside by the automated review system.

The pattern of more Inter Milan possession but more dangerous Fluminense chances continued early in the second half, and Sommer reacted superbly in the 62nd minute to dive and push Arias’s effort from beyond the penalty area just around his left post.

Lautaro Martinez came closest to pulling Inter Milan level, forcing the 44-year-old Fabio into a pair of saves in the 80th and 82nd minute, then striking the post with another low effort only seconds later.

Eleven minutes later, Inter Milan’s at times shaky defence was exposed for a second time. Hercules found himself free at the edge of the 18-yard box following a throw-in, and he drove a composed, low finish into the bottom right corner and sent the Fluminense fans into delirium.

Fluminense captain Thiago Silva said he was “very proud of my team and teammates” for beating such a top side and in extremely hot conditions.

“I’m very happy for myself and the team,” he told DAZN. “Ten days ago, I had an injury, and it wasn’t easy to play today. But I am very happy with the medical team … it was very very important for me to play today.”

The result ensured that there will be two Brazilian quarterfinalists in the first edition of this expanded tournament format, after Palmeiras also reached the last eight.

Fluminense will play the winner of Monday’s later game between Manchester City and Al Hilal in the quarterfinals.

If heavily favoured Manchester City progress, it would present a rematch of the 2023 Club World Cup final, which Manchester City won 4-0.

Inter Milan were eliminated in the second round 30 days after they suffered a 5-0 defeat to Paris Saint-Germain in the UEFA Champions League final. They also narrowly finished second in the Italian Serie A.

Cristian Chivu, Inter Milan’s coach, hailed his team for their attitude as they battled to come back from conceding such an early goal.

“We didn’t give up; we tried until the end. We tried to make some changes even in the formation. It wasn’t our day,” he told DAZN.

“We didn’t expect them to play five at the back, but they were well organised with the low block on defence. It was tough for us to find solutions, especially in the first half when we tried a lot … in the second half, maybe we tried to switch a little bit more, to play outside and with some more crosses.

“We also tried to build something with two strikers in a 4-4-2. Until the end, we tried, but it wasn’t our day.”

Defending champion Taylor Fritz won two matches in one day by battling through “crazy” windy conditions at Eastbourne.

After Fritz’s second-round tie with 18-year-old Brazilian Joao Fonseca was suspended at 6-3 6-7 (5-7) for bad light on Wednesday, the pair resumed on Thursday afternoon, with Fritz edging the deciding set 7-5.

That match finished at 12:47 BST – and four hours and 23 minutes later Fritz returned to centre court to face Marcos Giron in the quarter-finals.

Fritz came through 7-5 4-6 7-5 against his American compatriot to reach the last four.

“I love this tournament. I’ve been very lucky to not play in very windy conditions,” Fritz, a three-time champion in Eastbourne, said.

“It’s tough for me when I don’t get to play the tennis that I love to play here. I have to scrap and play crazy tennis when it’s windy.

“I’m obviously really glad to get through it.”

Fritz, who beat world number three Alexander Zverev in the Stuttgart Open final 11 days ago, is among the favourites for the Wimbledon title.

He faces world number 28 Alejandro Davidovich Fokina in Friday’s semi-final after the Spaniard beat Czech Jakub Mensik 6-4 7-5.

Evans, who has a main-draw wildcard for Wimbledon, has just returned to the top 200 after a difficult few years.

The Englishman managed his nerves as the tension built against Paul. Evans hit just 17 winners to the American’s 31, but he also committed 26 unforced errors compared to Paul’s 43.

He will aim to be even more clinical when he faces American lucky loser Jenson Brooksby in the quarter-finals.

Earlier, Billy Harris continued his recent Eastbourne joy as the Englishman reached the quarter-finals for the second successive year.

Harris, who reached the main draw as a lucky loser having lost in qualifying, beat Italian qualifier Mattia Bellucci 6-3 6-4.

Harris will face French fourth-seed Ugo Humbert next and could potentially meet Evans in the semi-finals.

But British number two Jacob Fearnley suffered a chastening defeat by Marcus Giron.

The American dispatched Fearnley 6-3 6-1, with the Scot hitting five double faults and losing his serve five times.

Wimbledon begins on 30 June.

All eyes have been on Draper this week as he takes on the pressure of being the great British hope with Wimbledon approaching at the end of this month.

The 23-year-old has said he is comfortable dealing with that weight of expectation, and underlined that belief with this battling display.

He did, however, start slowly as a run of 11 consecutive points for Popyrin – briefly interrupted by an unexpected sudden gust of wind that sent a hat and bits of paper on to the court – led to the Australian taking the first set.

It was the second match in a row where Draper has taken his time to get into his groove and he revealed he had been struggling a bit with illness this week.

“I’ve not been feeling great actually, to be honest, the last day and a half,” he told BBC Sport.

“I was a bit flat out there. My body feels good but I was a bit under the weather.”

Draper will have his eyes firmly set on claiming a maiden title at Queen’s but he will have another incentive to keep progressing as reaching the semi-finals will mean he is seeded fourth at Wimbledon.

That would mean avoiding facing the likes of defending champion Carlos Alcaraz and world number one Jannik Sinner.

“It’s obviously a big thing,” Draper said. “I think it would definitely help. But at the same time, I don’t think I will think about that at all.

“I can’t control who I’m playing, can’t control any of those things, but I can control what I do between now and the next match, and I’ll prepare the best I can.”