France's Richard Gasquet ended Andy Murray's Masters Cup hopes by beating the British number one 6-3, 0-6, 6-4 in the Paris Masters Series quarter-finals on Friday.
Gasquet, who recovered from a second-set collapse, is now ideally placed to win the last remaining ticket to the November 11-18 season finale in Shanghai featuring the world's top eight.
The only other player left in the hunt is Cypriot Marcos Baghdatis, who earlier knocked Spaniard Tommy Robredo, out of the race, with a 6-4, 6-4 win.
Russia's Mikhail Youzhny also dropped out of contention on Friday with a 6-4, 6-2 defeat by world number two Rafael Nadal.
Gasquet will qualify for the Masters Cup if he makes the final or if Baghdatis loses to Nadal in Saturday's semi-finals.
Baghdatis will book a trip to China only if he wins the title and Gasquet is not in the final.
Murray netted a backhand to drop serve in the eighth game of the first set. Gasquet then served for the set, wrapping it up with a clever dropshot.
However, a string of unforced errors meant the Frenchman did not win a game in the second set which he lost to an opponent playing close to perfection.
WOKE UP
Unfortunately for Murray, Gasquet woke up in the decisive set, getting the telling break with a raging smash in the third game and staying in control until the Scot fired a return long on the second match point.
"I had three bad games in the whole match," said Murray, who had signalled his return to form by winning his third career title last Sunday in St Petersburg.
"It's disappointing when you win more games and more points than your opponent and end up losing the match," added the 20-year-old, who was sidelined for over three months this year with a wrist injury.
"After what I've been through this year, not making it to Shanghai is not a disaster," he added.
Standing in Gasquet's path to the final is Argentine David Nalbandian, whose Shanghai hopes ended on Thursday despite his third-round victory over world number one Roger Federer.
The unseeded Nalbandian, who had beaten Federer in the Madrid Masters final late last month, needed three sets and nearly as many hours to down Spain's David Ferrer 7-6, 6-7, 6-2 in a ferocious contest featuring thrilling rallies.
Fifth seed Ferrer, who has already qualified for Shanghai, matched his opponent's power and determination for two sets but ran out of steam and Nalbandian wrapped it up with an ace.
