Former world number one Andy Murray was knocked out in the last-16 of the second-tier Challenger in Rennes on Wednesday as the three-time major winner continued his search for late-season momentum.
Murray, now down at 116 in the world, lost to 158th-ranked Roman Safiullin of Russia, 6-2, 4-6, 6-1.
The 34-year-old Murray, pushed to the brink of retirement in 2019 by a hip injury, managed to save three match points before succumbing.
Murray had defeated Germany's Yannick Maden 6-3, 6-1 in the first round on Monday in front of around 2,000 fans.
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Just two weeks earlier, he had been playing on the 24,000-capacity Arthur Ashe Court in New York, losing a fiery five-setter to Stefanos Tsitsipas in the first round of the US Open.
"One of the goals between now and the end of the year is to try and make a big improvement with my ranking, and to do that, I need to be competing often," said Murray earlier this week.
"I still feel like I can play a very high level, but if all of the time when I go to the big tournaments I play top players right at the beginning of the event, it's not so easy."
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