Novak Djokovic hampered by hip injury as history-maker Valentin Vacherot reaches Shanghai Masters final

Novak Djokovic's gutsy efforts were in vain as the 24-time Grand Slam winner fell to a semi-final loss to Monegasque trailblazer Valentin Vacherot in the Shanghai Masters.

The 38-year-old struggled with a hip injury throughout the contest and succumbed to a 3-6 4-6 loss to the world number 204, whose magical and historical run at the ATP 1000 tournament continues.

Djokovic had been hampered by leg and foot issues during his progression to the final four, and with just a few games gone in Saturday's semi-final, the 100-time ATP Tour singles title winner was moving gingerly with a hip concern.

The Serbian superstar repeatedly stretched the ligament in between points, but he refused to throw in the towel and at one stage looked capable of pulling off a tremendous comeback against the lowest-ranked opponent he had ever faced in a top-level semi-final.

However, Djokovic's physical condition proved too challenging for the veteran to overcome, as the big-serving Vacherot prevailed in one hour and 42 minutes to become the first ever male player from Monaco to reach a Masters singles final.

At the same time, the world number 204 denied Djokovic the chance to compete for a record-extending 41st ATP 1000 crown, and he could remarkably face his cousin Arthur Rinderknech in the showpiece match if the Frenchman can stun Daniil Medvedev in the second semi-final.

How Valentin Vacherot took down injured Novak Djokovic in Shanghai semi-final

Valentin Vacherot historic run continues ?

He upsets Novak Djokovic to reach Rolex Shanghai Masters final ? pic.twitter.com/yAGfYxaBaM

— Sky Sports Tennis (@SkySportsTennis) October 11, 2025

Vacherot had already made a habit of upsetting notable names in Shanghai, as Holger Rune, Tallon Griekspoor and Alexander Bublik - all of whom were seeded for the tournament - fell to his superiority in the earlier rounds.

The underdog could hardly have got off to a worse start on Saturday, though, as Djokovic broke his foe to 15 in the opening game, but Vacherot responded straight away before the Serbian's body began to fail him.

Djokovic nevertheless soldiered on through the pain - with the help of a few medical timeouts - but he lost serve again in the eighth game before Vacherot held to love to see out the first set.

The 24-time major winner sparked hope of a magnificent fightback at the start of the second set, saving two break points to hold in a lengthy opening game, but Vacherot shut the door on any break opportunities for the world number five.

A spate of double faults in the penultimate game then proved fatal for Djokovic, whose three such mistakes presented Vacherot with the chance to serve for a place in the Shanghai final.

After one break point and one match point went begging on either side, Vacherot produced two trademark venomous serves to send Djokovic home and become the lowest-ranked Masters finalist since the format's inception.