Jelena Dokic was stunned 6-7, 3-6 by Mara Santangelo of Italy in the first round of the WTA Hyderabad Open on Tuesday.
The former world number four hardly looked in the game after surrendering the first set.
The unseeded Serbian, who had withdrawn from last week's Volvo Open in Pattaya, Thailand, due to a groin strain, struggled with her serve and was broken in the first game in both the sets.
Down 0-3 in the first set, she broke back in the fifth game with a couple of scorching winners and leveled the match 3-3. The 21-year-old, who has slipped out of the top 200, then did well to take the set to the tie-break, but Santangelo proved too accurate for her.
The last game of the first set saw three close calls go against Santangelo but she kept her cool to clinch the tie-breaker 7-2, serving out the set with a couple of forehand winners.
Dokic served two double-faults in the tie-break and lost interest in the match after that.
She was broken twice in the second set. Santangelo also had her a break point down in the seventh game of the set, but the Serbian warded it off and won the game.
The struggle continued in her next service game as, at 15-40, she stared down at two match points.
Throughout the match Dokic caught up with Santangelo and it looked like she would fight her way back when the scores edged to deuce. But on the third match point down, she hit a return long to hand the match to the Italian, who, in the end, was rewarded for her patience.
Both the players refused to appear at the post-match conference. Dokic was fined $2500 in 2000 by the Women's Tennis Association when she failed to turn up for a press conference on time after her first round defeat to Rita Kuti-Kis at the Australian Open.
Top seed Na Li of China, playing on an outside court, defeated Switzerland's Marie-Gayanay Mikaelian 6-3, 6-3 to enter the second round.
In the other first round matches, 18-year-old Maria Kirilenko of Russia beat compatriot Tatiana Poutchek 6-3, 6-1 and Slovakia's Jarmila Gajdosova overcame qualifier Ting Li of China 6-3, 6-2.