Somdev Devvarman suffered a second successive defeat against Serbia's Janko Tipsaveric to crash out of the ATP Farmers Classic.
The Indian qualifier fought hard but lost 6-7 (9), 2-6 to his sixth seed and world number 46 rival in the second round of the $619,500 hard court event.
Somdev, ranked 103, had lost to Tipsaveric at Chennai Open earlier this year in the pre-quarterfinals.
Somdev collected useful 20 points by making the second round apart from 12 points from the qualifiers.
These 32 points have enhanced Somdev's chances to break into top-100 for the first time in his career.
Leander Paes was the last Indian to feature in singles top-100 way back in 1999.
A top-100 place will also help Somdev earn a direct entry into men's singles main draw of the US Open, the last Grand Slam of the season.
Meanwhile, Rohan Bopanna and Pakistani partner Aisam-ul-Haq Qureshi have progressed to doubles quarter-finals after beating British pair of Colin Fleming and Ken Skupski.
The fourth seed Indo-Pak pair faced a stiff competition before scoring a 6-7(3), 6-0, 10-7 win in the opening round.
