Second seed Somdev Devvarman crashed out of the Tashkent ATP Challenger after a straight-set defeat against Milos Raonic, placed 60 places below him.
The 95th ranked Indian, who came into the tournament after winning singles gold in the Commonwealth Games, lost 4-6 6-7(5) to Canadian in the second round.
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Somdev earned 10 ranking points and USD 2150 as prize money.
Another Indian bowing out was Purav Raja, who lost the doubles quarterfinal along with Australia's Sadik Kadir. They lost 6-3 1-6 8-10 to fourth seeds Treat Conrad Huey of Philippines and British Dominic Inglot.
Raja and Sadik got 25 points each and split USD 1600.
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