Joao Sousa and Borna Coric were both knocked out in the opening round of the Open Sud de France on Tuesday evening.
Seeded sixth, Sousa fell to Belgium’s Ruben Bemelmans 4-6, 6-3, 6-4 on the hard courts of the French city.
The duo traded breaks before Bemelmans broke serve one last time to clinch the opening set.
The Portugal native bounced back in the second set courtesy of a break of serve to set up a decider.
Sousa fought off two match points at 5-3 to get back on serve in the third set, but then Bemelmans battled back one last time to break him and secure the victory.
Seventh seed Borna Coric was knocked out by Michael Berrer, losing 7-6(5), 6-2 in 81 minutes.
The pair swapped service breaks to force a tiebreaker. Coric looked on track to seal the set at 5-3 up, but the German rallied to win the final four points.
Berrer then turned on the class to break Coric twice en route to booking his place in the second round.
In other results, Jan-Lennard Struff defeated local favourite Nicolas Mahut 6-3, 7-5 while french duo Kenny de Schepper and Paul-Henri Mathieu advanced to the next round with wins over Nikoloz Basilashvili and Elias Ymer respectively.