Andy Murray was beaten 6-4 6-2 as he was knocked out of a clay-court ATP Challenger event in Bordeaux by Gregoire Barrere.
Murray went 5-0 down in the first set and, despite recovering to 5-4, Frenchman Barrere then held his serve to take the opener.
The Briton, who is 77th in the rankings, was broken to love in the third game of the second set and, after failing to take two break points in the next game, went 3-1 down.
Barrere, ranked 115 in the world, went on to lead 5-2 before serving out to win the match in one hour 27 minutes.
Overall, Murray took three of six break points, while his opponent converted six from seven.
The tournament was 37-year-old Murray’s first since he ruptured ankle ligaments suffered at the Miami Open in March and he came through a first-round match after opponent Kyrian Jacquet retired when trailing in the second set.
Three-time Grand Slam champion Murray has previously said he does not plan to “play much past this summer” but has not announced where his final tournament will be.
Briton Dan Evans is also taking part in the competition and won 6-3 7-6 (7-3) against Frenchman Harold Mayot to progress to the quarter-finals.
Evans will play Shang Juncheng of China in the next round.
