Ramanathan, Singh and Sasikumar shown the door in first round.
Third seed Duje Ajdukovic and the trio of Indian players, including Ramkumar Ramanathan and Mukund Sasikumar, were knocked out in the men's singles opening round of the Chennai Open ATP Challenger in Chennai on Tuesday.
However, the tournament's top seeds Billy Harris and Lloyd Harris started their campaigns on a winning note.
Ajdukovic, ranked No. 158 in the world, lost 2-6, 7-6, 2-6 to 332-ranked Swedish player Elias Ymer.
It was not a good day for Indian singles players at the SDAT Tennis Stadium either with all the three local players exiting in the first round.
21-year-old Karan Singh was defeated 3-6, 3-6 by Frenchman Kyrian Jacquet, while Ramkumar went down to Great Britain's Jay Clarke 3-6, 5-7.
Sasikumar was able to force a decider, before eventually falling to Alexey Zakharov 3-6, 7-6, 1-6.
In the doubles draw, Indian pair Siddhant Banthia and Parikshit Somani beat compatriots Sai Karteek Reddy Ganta and Vishnu Vardhan 6-3, 3-6, 10-7 to book their spot in the quarter-finals.
Top seed Billy Harris of Great Britain and second seed Lloyd Harris of South Africa were among the seeded players who advanced to the second round.
Billy defeated Ukrainian qualifier Eric Vanshelboim 7-5, 6-2 while Lloyd, a former US Open quarter-finalist, overcame another Ukrainian qualifier Yurii Dzhavakian 6-3, 5-7, 6-0.
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