Yuki Bhambri made a forgetful comeback from injury as he failed to cross the first hurdle at the Singapore Open on Wednesday.
The Indian was beaten in straight sets by Australia's Matthew Ebden 6-3, 7-6 (7-3).
In the first set, Bhambri, playing his first competitive game in over two years, started well but the rustiness was there to see as he allowed Ebden to break his serve early in the encounter.
In game nine, Bhambri's serve was once again broken and the Aussie pocketed the first set with ease.
In the second set, Ebden was in no mood to relent, gaining nearly break. In imperial form, Ebden made the Indian toil hard for each point.
Bhambri though did not relent easily, breaking for the first time in the match to narrow down the scoreline to 5-4.
He backed it up by holding his serve to come back into the set. However, in the tie-breakers, Ebden regained his composure to oust the Delhi-born player from the tournament.
The match marked Bhambri's return to the tour after a long hiatus. The Indian last played a competitive match in October 2018 and had been forced out since with a knee injury.
On the other hand, the Indian pair of Ramkumar Ramanathan and Purav Raja was handed a walkover by their opponents Yasutaka Uchiyama and Kwon Soon-Woo.
Ramanathan and co. have now booked their place in the quarter-finals and are set to lock horns against top-seeded Belgian pair Joran Vliegen and Sander Gille.
In the Round of 16, they blew away Evan King and Hunter Reese in straight sets. Vliegen is currently ranked 37th in the world, whereas his partner Gille stands four places behind him on 41.
It will be a stiff challenge for the Indian duo to get the better of their more illustrated opponents and progress to the semifinals.