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While Vishnu Vardhan and Karanuday Singh fought well before losing, Rupesh Roy hardly troubled his opponent.
Vardhan, who won mixed doubles gold with Sania Mirza at Asian Games, came back strong from the first game drubbing but lost 1-6 4-6 to Ante Pavic of Croatia.
Singh went down fighting 3-6 5-7 against world number 120 Go Soeda of Japan. Roy was ousted by 3-6 1-6 by Konstantin Kravchuk of Russia.
In a game that was a battle between two baseliners, Singh struggled to return Soeda`s serves and lost the first set 3-6.
However, the 20-year-old Indian came back strongly in the second and went 5-4 up after trailing 2-4.
Soeda made too many unforced errors but Singh could not cash on his rival`s shortcomings and the Indian lost the game 5-7 from having a good chance to level the match.
Vardhan, who upset third seed Conor Niland in the first round yesterday, made a horrible start as he lost first set 1-6 to Pavic. He raised his game after that but had no answer to the power hitting of the tall Pavic.
Another person of Indian origin, Rajeev Ram lost 0-6 6-4 5-7 to Alexandre Kudryavtsev of Russia.
Kudryatsev will meet Pavic for a spot in the main draw on Monday, while Kravchuk will meet Yuichi Sugita of Japan.
Results: Milos Raonic (CAN) bt Evgeny Kirillov 6-2 7-5; E R Vasselin (FRA) bt Skugor (CRO) 6-4, 3-6, 6-3; Go Soeda (JPN) bt Karunuday Singh (IND) 6-3, 7-5; Konstanstin Kravchuk (RUS) bt Rupesh Roy (IND) 6-3 6-1; Yuichi Sugita (JPN) bt Leos Friedl (CZE) by walk over; Ivo Minar (CZE) bt David Goffin (BEL) 6-4, 6-3; Ante Pavic (CRO) bt Vishnu Vardhan (IND) 6-1, 6-4; Alexandre Kudryavtsev (RUS) bt Rajeev Ram (USA) 6-0, 4-6 7-5.
