British men's number one Cameron Norrie saw his hopes of qualifying for the ATP Finals take a blow after a straight-set loss to American Taylor Fritz in Paris.
Fritz won 6-3 7-6 (7-3) to progress to the last eight, where he will face world number one Novak Djokovic.
Significant points are on offer in Paris in the hunt for a spot in the year-end ATP Finals.
Norrie, 26, could have guaranteed qualification with a title win.
Both players played exceptional tennis as the match went to a tie-break in the second set.
Fritz continued his recent fine run of form to see off a battling Norrie, with the American producing a strong service game throughout, hitting 10 aces to the Briton's three.
Norrie has reached six finals this year, including his title success at the prestigious Indian Wells event last month, with his form seeing him rise from 74th in the world rankings to 13th.
There are two remaining spots at the ATP Finals in Turin, where only the best eight qualified singles players compete - though this defeat has diminished his chances.
Norway's Casper Ruud and Poland's Hubert Hurkacz are both ahead of Norrie, with Hurkacz adding another 90 points to his total after a 4-6 7-5 6-2 last-16 win over Germany's Dominik Koepfer in Paris.
Norrie trails Hurkacz by 190 points in the battle for qualification.
Djokovic progressed to the quarter finals without lifting a racket after his last-16 opponent, Gael Monfils, withdrew due to a leg injury sustained during his second-round win over fellow Frenchman Adrian Mannarino.
Australia's James Duckworth defeated his countryman Alexei Popyrin 7-6 (8-6) 6-4 to reach his first Masters quarter-final, where he will face Hurkacz.
In the doubles, Britain's Jamie Murray progressed to the last eight with Brazilian Bruno Soares, defeating Spain's Roberto Bautista Agut and Alexander Bublik 6-1 6-3.