Novak Djokovic lost on his return to competitive tennis to Taro Daniel in the BNP Paribas Open at Indian Wells.
Daniel, ranked 109 in the world, claimed the biggest win of his career as the qualifier prevailed 7-6 (7/3) 4-6 6-1.
Japan's Daniel won the first set on a tie-break before Djokovic, making his return from an elbow injury, took the second.
However, 25-year-old Daniel dominated the third and final set to take it 6-1.
Daniel, who beat Britain's Cameron Norrie in the first round, will meet Leonardo Mayer, who beat Ruben Bemelmans 6-4 6-1.
British number one Kyle Edmund was beaten in straight sets by Israel's Dudi Sela 6-4 6-4 in his first match since reaching the Australian Open semi-finals.
Edmund, who has been out of action with a hip injury since his brilliant performance in Melbourne, led 3-1 in the opening set and had two break points to go further ahead.
However, world number 97 Sela dug deep to hold serve and immediately broke Edmund to get back on level terms before another break in the 10th game secured the set.
Sela also took the second set by the same score to seal a 6-4 6-4 victory in 91 minutes against world number 24 Edmund, who replaced the injured Andy Murray as British number one earlier this month.
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Novak Djokovic's Australian Open participation is in doubt after he was forced to withdraw from an exhibition event in Abu Dhabi with an elbow injury.
The Serbian has been out for almost six months and had been due to make his return to action at the World Tennis Championship.
However, he has now pulled out of a scheduled match against Roberto Bautista Agut and admits the injury "might affect the start of the season", with the Australian Open starting on January 15.
Andy Murray, who had been at the event just with the intention of training as he recovers from his own injury problems, will now step in to face Bautista Agut, according to a post on the tournament's Facebook page.
Novak Djokovic will make his return to tennis in Abu Dhabi at December's World Tennis Championship.
The Serbian has skipped the back end of the current season because of an elbow injury, playing no part since abandoning his Wimbledon quarter-final against Tomas Berdych in July.
But 30-year-old Djokovic will return for the 2018 campaign, and the 12-time grand slam winner is planning an early start with an appearance at the December 28-30 exhibition tournament in the United Arab Emirates.
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