Pain for Alex de Minaur as fans blown away by moment never seen before in 16 years

Alex de Minaur is rueing another missed opportunity against a top opponent, amid a stunning run by a pair of cousins who have re-written the tennis history books. De Minaur has risen to World No.7 on the back of some stellar form in recent weeks, but lost in the quarter-finals at the Shanghai Masters on Friday night.

The Aussie star went down 6-4 6-4 to Daniil Medvedev - the eighth time in 12 meetings he's lost to the resurgent Russian. Medvedev almost looked out on his feet as he struggled with cramp against Learner Tien in the fourth round, but against de Minaur he again resembled the man who once made it to World No.1.

It was heartbreak again for de Minaur as he looked to score the 300th tour-level win of his career. The Aussie gave himself six break-point chances, only to be repelled on each occasion by the 29-year-old 'Octopus'.

"I was super tired. I knew against Alex, like Learner, we were going to get a lot of long points," Medvedev said afterwards. "We had a couple in the that first set (of 29 strokes), and I knew it was going to be a long day.

"But I'm happy about the way I played. I was really clutch in important moments, hitting the ball great and putting him under pressure many times. I'm really happy with this level."

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For de Minaur it was another story of what might have been in Masters events. He's only made one Masters final in his career and always seems to come unstuck against elite opponents. Last week at the China Open he made the semi-finals, only to lose to Jannik Sinner for the 11th time in 11 meetings.

Little-known cousins make tennis history in Shanghai

Even more frustrating for de Minaur was that he would have have had the chance to face a lowly-ranked opponent in the semis. Frenchman Arthur Rinderknech caused a huge boilover against 12th seed Felix Auger-Aliassime, winning 6-3 6-4 to make the final four.

The World No.54 joins his even more unheralded cousin Valentin Vacherot in the semis, after the World No.204 from Monaco had earlier shocked Danish 10th seed Holger Rune. In doing so, Vacherot became the second-lowest ranked player ever to reach a Masters 1000 semi-final.

The cousins' march into the semis marks the first time in the 16-year history of the Shanghai Masters that two players from outside the top-50 have made the final four. It's the first time in all Masters 1000 events on hard court since Paris 2017.

There's every chance the cousins could face off in the final, although Vacherot has to get past Novak Djokovic in his semi. Rinderknech will face Medvedev for a spot in the title match.

"First of all, I follow my cousin. He's going through the emotions, and I'm trying to battle to follow and do as good as him," Rinderknech said as Vacherot cheered him from the stands. "It's been incredible since the beginning of the week, the whole family following from home. We are in our little world of our own.

"It's been incredible, it's been unreal. It's been a good performance from myself - happy to get the win, two sets so I can be not too tired for tomorrow."

At age 30, Rinderknech is the oldest first-time Masters 1000 semi-finalist since Jan-Lennard Struff of Germany achieved the feat in Madrid in 2023. Tennis fans and commentators have been blown away by the remarkable run from the little-known cousins.

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