Swiss Roger Federer is out of the Shanghai Rolex Masters after losing his third-round match in three sets against Frenchman Gael Monfils.
The 17-time Grand Slam champion and seventh seed lost 6-4, 6-7 (5-7), 6-3, to his unseeded opponent.
Federer, 32, now faces an uphill task to reach the season-ending ATP World Tour at the O2 Arena in London with the Swiss Indoors and the Paris Masters being the remaining tournaments he is due to compete at as he bid to make up the points in the ATP Race.
Playing in his first tournament since losing in the fourth-round of the US Open, he had been desperate to improve on his dismal performance so far this season.
But against the 42nd ranked Monfils, he rallied from a break down in the second set and 5-3 down in the tiebreaker, but couldn’t recover after being broken early in the deciding set.
Monfils, 27, will next meet the winner of the match between Novak Djokovic and Italian Fabio Fognini
Elsewhere France’s Jo-Wilfried Tsonga moved into the quarter-finals with a 7-6(7-5), 6-0 win over Japan’s Kei Nishikori.
Tsonga next meets Germany’s Florian Mayer who was too good for David Ferrer.
Mayer saw off David Ferrer 6-4, 6-3, although the Spaniard, alongside Rafael Nadal and Djokovic, has already qualified for the ATP World Tour as top three seeds in the absence of Andy Murray.
Nadal moved into the quarter-finals of the Shanghai Masters in China with a 6-1, 7-6 (7-5) victory against Argentina’s Carlos Berlocq.