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Britain’s Andy Murray fell to a straight-set defeat against Russian fifth seed Andrey Rublev in the third round at Indian Wells.
Three-time Grand Slam champion Murray, 36, was beaten 7-6 (7-3) 6-1 by Rublev in a high-quality match in California.
Murray, who has said he is not planning to “play much past this summer” as he considers retirement, missed four set points when leading the first set 5-4.
He then quickly faded in the second after losing serve in the fourth game.
Murray, who finished runner-up to Rafael Nadal at the tournament in 2009, thanked the Indian Wells crowd on what he acknowledged would be his final visit.
“I’ve loved coming to this place over the years,” he said, praising the support from fans which had allowed him “to play in some amazing atmospheres and create brilliant memories – because without them it’s not the same”.
Elsewhere, Australian Open champion Jannik Sinner progressed with a straight-set victory over Australian Thanasi Kokkinakis.
The Italian world number three, 22, took just 81 minutes to seal a 6-3 6-0 win and will play German Jan-Lennard Struff or Croatia’s Borna Coric in the third round.
Defending champion Carlos Alcaraz, the second seed, dropped the first set against Italy’s Matteo Arnaldi but the Spaniard recovered to win 6-7 (7-5) 6-0 6-1.
German sixth seed Alexander Zverev won 6-4 6-4 against Australia’s Christopher O’Connell, while Greek 11th seed Stefanos Tsitsipas defeated French qualifier Lucas Pouille 6-3 6-2.
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