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Indian Davis Cupper Somdev Devvarman won the first set, but squandered the lead en route to a first-round loss in the ATP Challenger in Calabasas, US.
He went down 6-4, 4-6, 3-6 to local favourite Alex Bogomolov.
However, his doubles campaign is yet to start.
Somdev has teamed with Australia's Nathan Healey and the qualifier duo will open their challenge against the third seeded South African-American pair of Izak Van der Merwe and Todd Widom.
The tournament also features Prakash Amritraj, who advanced to the second round on Tuesday.