Somdev Devvarman went down fighting against world number 54 Mikhail Kukushkin in the quarter-finals of the USD 100,000 ATP Challenger event here.
Somdev, currently ranked 147 after a string of poor performances, lost to the top seeded Kazakhstan player 5-7 6-4 2-6 after battling for close to two hours.
It was second meeting between the two players and the Indian had emeregd winner when they clashed in 2011 in Belgrade, Serbia.
Somdev earned 18 ranking points and USD 2,920 as prize money for his effort.
Meanwhile, Sanam Singh and Purav Raja advanced to the doubles semifinals of the same tournament with a 7-6(4) 6-2 win over Andrea Collarini from Argentina and Mexico's Cesar Ramirez.
The fourth seeded Indian pair will next play top seeded American-Australian combo of Austin Krajicek and John-Patrick Smith.