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He is the last player to defeat Jannik Sinner at a Masters 1000 event over seven months ago

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Jannik Sinner booked his place in the Madrid Open round of 16 with a straight sets win against Elmer Moller.

Sinner rarely looked fazed during Sunday’s contest, defeating his Danish opponent 6-2, 6-3.

The Italian, who recently reclaimed the world number one spot from Carlos Alcaraz, is seeking to become the first man in tennis history to win five consecutive Masters 1000 events.

Jannik Sinner of Italy plays a backhand against Elmer Moller of Denmark during the 2026 Mutua Madrid Open Men's Round of 32 match on Day Seven at La Caja Magica on April 26, 2026 in Madrid, Spain.
Photo by Mateo Villalba/Getty Images

Following his victory over Moller, Sinner has now won 24 consecutive Masters 1000 matches, dating back to October 2025.

So, who was the last player to defeat the imperious Italian at Masters 1000 level?

Tallon Griekspoor is the last player to defeat Jannik Sinner at an ATP Masters 1000 tournament

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2025 French Open - Day Fifteen
Photo by Andy Cheung/Getty Images

Carlos Alcaraz was not competing in the Shanghai Masters, making Sinner the runaway favourite to win his second title at the event.

Sinner began the event in his usual imperious fashion, comfortably defeating Daniel Altmaier 6-3, 6-3 in his opening match.

However, in the third round, Sinner’s hopes of winning the event were quashed.

Jannik Sinner’s record at Masters 1000 events since the 2025 Shanghai Masters

Sinner took an early lead against Dutch 27th seed Tallon Griekspoor, winning the opening set 7-6.

However, Sinner began to suffer from cramping amid soaring temperatures and extreme humidity.

The Italian, unable to walk at times, was forced to retire from the match while trailing 7-6, 5-7, 2-3.

“This is definitely not the way you want to win,” said Griekspoor after the contest, as per The Guardian.

Italy's Jannik Sinner (R) reacts as he retires from his men's singles match against Netherlands' Tallon Griekspoor (L) at the Shanghai Masters tennis tournament in Shanghai on October 6, 2025.
Photo by Hector RETAMAL / AFP via Getty Images

“Brutal conditions here in Shanghai all week already. I thought we were still a little bit lucky to play in the evening without sun, but two hours, 36 minutes on the clock, middle of the third set.

“Sorry for him, I wish him a speedy recovery.”

“The first set was high quality from both, very dominant in the service games.

“I thought he played an unbelievable tie-break: He hit a couple of lines, served really well.

Tallon Griekspoor of Netherlands competes against Jannik Sinner of Italy in the Men's Singles 3rd round match on day 7 of the 2025 Shanghai Rolex Masters Qi Zhong Tennis Center on October 05, 2025 in Shanghai, China.
Photo by Hu Chengwei/Getty Images

“I got a bit lucky at 3-4 in the second, where I saved 0/40 and served my way out of it. Sometimes you need a little bit of luck to win these matches.”

Sinner said the cramps were due to a ‘mental factor’

Two weeks after his retirement, Sinner offered an explanation for his cramps while in conversation with Italian outlet Cronache Spogliatoio.

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Jannik Sinner waves with his Miami Open trophy
Photo by Carmen Mandato/Getty Images

“The cramps in Shanghai? I think they were due to a mental factor,” said Sinner, as reported by TNT Sports.

“I talked with my team, from that point of view I wasn’t perfect, but now everything’s fine. The mistake was mine.

“The heat and humidity got me down.

“You learn from these things. Cramps can happen, and I was one of many to suffer from them.”

Jannik Sinner of Italy withdraws due to injury during the match against Tallon Griekspoor of Netherlands in the Men's Singles 3rd round match on day 7 of the 2025 Shanghai Rolex Masters Qi Zhong Tennis Center on October 05, 2025 in Shanghai, China.
Photo by Hu Chengwei/Getty Images

As evidenced by his recent results, Sinner did not let his Shanghai loss affect him for too long.

The Italian has gone on to dominate the Masters 1000 scene, winning the last four available titles.