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.
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.