Novak Djokovic has continued his struggles into Indian Wells, where he has lost his opener to Botic van de Zandschulp.
Djokovic was backed to reach the semi-finals of Indian Wells this time around, but the sixth seed fell in the round of 64.
The Serbian has won five Indian Wells titles, the joint-most alongside Roger Federer, with 99 ATP titles to his name.
But Djokovic has been sent home early by Van de Zandschulp, who secured a shock 6-2, 3-6, 6-1 victory.
His search for an elusive 100th ATP title will, therefore, continue, with his latest defeat following a round of 32 loss at the Qatar Open.
Novak Djokovic joins Rafael Nadal on 500 ATP Masters 1000 matches
Despite his early Indian Wells exit, Djokovic has managed to emulate his fellow legendary figure Rafael Nadal.
As per OptaAce, Djokovic appeared in his 500th ATP Masters 1000 match, equalling Nadal (500) for the most since the format’s introduction in 1990.
Bastien Fachan then shared the pair’s record at this level, with Nadal having posted 410 wins and 90 losses.
Djokovic meanwhile has a record of 409 and 91 respectively, which can still be improved upon given his ambitions to continue playing.
Novak Djokovic certain to be disappointed by shock Indian Wells loss
It has been quite the season so far for Djokovic, who was left as the last of the Big Three when Nadal retired late last year.
He remains top of the pile when it comes to Grand Slam titles, with his 24 ahead of Nadal (22) and Roger Federer (20).
But further success has been hard to come by so far, with the Serbian beginning his 2025 by losing in the Brisbane International quarter-finals.
He did, however, once again prove his worth at Grand Slam level at the Australian Open, only to retire hurt in his semi-final with Alexander Zverev.
His wait for another trophy now goes on, with the 37-year-old certain to be disappointed with the manner of his Indian Wells exit.
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