Novak Djokovic's injury nightmares continued on Saturday as he crashed out of the Shanghai Masters in a stunning defeat to world No. 204 Valentin Vacherot. The Serbian legend was chasing his first Masters 1000 crown since Paris nearly two years ago.

The path had seemingly cleared for Djokovic with world No. 1 Carlos Alcaraz withdrawing before the tournament began and world No.2 Jannik Sinner forced to retire during his last 32 battle against Tallon Griekspoor. World No. 3 Alexander Zverev also tumbled out - losing to eventual runner-up Arthur Rinderknech in the same round as Sinner.

However, Djokovic became the latest casualty of injury troubles after appearing to pick up a leg problem early in his semi-final showdown with Vacherot. The Serbian battled courageously but was visibly struggling against his Monégasque rival, who would claim the trophy 24 hours later.

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Following his victory over Djokovic, Vacherot heaped praise on his opponent while recognising the physical demands now facing the 38-year-old.

"I'm surprised by how I handled it mentally," he said post-match.

"Novak immediately broke my serve, playing just as I thought he would. I was delighted to break back as quickly as possible. Then it became a battle.

"We know Novak is 38 years old. It's already incredible what he is doing at that age, which is very tough for his body.

"The truth is, I had to stay focused. I had so many thoughts in my head, even when I had just won the first set and all."

"Still, every time I had small thoughts, I simply attributed them to thinking about the next return I was going to make or the next serve I was going to execute."

Djokovic's physical woes have been escalating for a while. The former world No.1 was forced to withdraw from Roland Garros mid-tournament last year due to a knee injury.

Separate issues cropped up in 2025, with Djokovic bowing out of his semi-final match against Zverev at the Australian Open in January due to injury. Another injury surfaced at Wimbledon as he hobbled to defeat against Sinner in the semi-finals.

Then, the 24-time grand slam winner appeared physically subpar in his semi-final defeat to Alcaraz at the US Open in September. Now, another injury has emerged which could signal the end of his 2025 season and edge him nearer to retirement.

Djokovic declined to respond to queries about his injury and forthcoming schedule when questioned after Saturday's loss to Vacherot.

"No. Next question, please," he retorted. On his opponent's famous victory, he said: "I want to congratulate Valentin for reaching his first Masters final. Going from qualifications, it's an amazing story.

"I told him at the net that he's had an amazing tournament, but more so his attitude is very good, and his game was amazing as well. So it's all about him. I wish him all the best in the finals, and the better player won today."