An ailing Novak Djokovic was knocked out of the Shanghai Masters semifinals on Saturday by world number 204 Valentin Vacherot.
The 26-year-old qualifier from Monaco beat Djokovic 6-3, 6-4 to deny him a record-extending fifth title in Shanghai.
A hobbling Djokovic, 38, threw up courtside and received medical treatment multiple times.
Vacherot will face either his cousin, the unseeded Frenchman Arthur Rinderknech, or Daniil Medvedev in Sunday's final.
"I'm trying to pinch myself, is this real," said Vacherot after the biggest win of his career.
"I know not many of you guys wanted me to win," he told the crowd, who had cheered thunderously for 24-time Grand Slam champion Djokovic.
"To have Novak on the other side of the court was first of all an invaluable experience for me.
"I have a hundred feelings right now."
Djokovic, the former world No 1, said Vacherot's unlikely run in the tournament was "an amazing story".
Vacherot is the lowest-ranked player to reach an ATP Masters 1000 final since the format's introduction in 1990.
"I told him at the net that he's had an amazing tournament, but more so his attitude is very good...so it's all about him," said Djokovic.
"I wish him all the best in the finals and the better player won today."
HEALTH ISSUES
Djokovic declined to answer questions about his physical state.
He had said after his last match that he was concerned after battling vomiting bouts, leg injury scares and fatigue throughout the tournament.
However, he looked alert and seemed to be having a dream start when he broke in the first game.
But the satisfaction was short-lived as Vacherot broke back instantly.
The Serb began having issues in his left leg at the start of the seventh game, stopping to stretch multiple times and dropping to the ground at one point.
He had to take an extended medical break, lying on his stomach shirtless as a physio attended to his back.
He got up but was still uncomfortable, hitting a ball against the wall in frustration after having to shake his leg out again.
With Djokovic clearly unable to move normally, Vacherot had an easy time breaking again in the eighth game, then fired two aces to hold the ninth and claim the set.
Djokovic received treatment again at the break, but was clearly still struggling in the second set.
In temperatures of 31 C and humidity levels of 62 per cent, Djokovic managed to hold the first game despite facing breakpoint twice and falling to the ground again.
Serving in the ninth game he hit two double-faults in quick succession before recovering, only to ultimately be broken upon committing another.
Despite a last-gasp effort from Djokovic, Vacherot held serve and his nerve to seal victory.
Never forget 🙌
— ATP Tour (@atptour) October 11, 2025
The moment @val_vacherot became an ATP Masters 1000 finalist.@SH_RolexMasters | #RolexShanghaiMasters pic.twitter.com/3bSecRk2bD