MELBOURNE, Australia-Novak Djokovic suffered his earliest Australian Open loss since 2006 on Friday when the six-time champion went down in a second-round upset to Denis Istomin 7-6 (10-8), 5-7, 2-6, 7-6 (7-5), 6-4.
Djokovic spent almost five hours in his struggle against a player who won an Asian qualifying competition for a spot in the draw. Istomin wrapped up the stunning victory on his first match point when Djokovic hit a return long.
Djokovic went down with 68 winners and 72 unforced errors to the No. 117-ranked player, whom he had dominated in their previous five encounters.
"From the third set I had cramp in my leg, I don't know how I held it," Istomin said. "I was playing so good. I surprised myself. I feel sorry for Novak. I was playing so good today."
Djokovic said: "Denis deserved to win. No doubt, he was a better player in the clutch moments. He stepped it up, played aggressive. Served very well, very precise. There's not much I could do.
"I was not pleased with my performance overall. But I have to congratulate my opponent today."
It marks only Djokovic's seventh loss in Melbourne against 58 wins and puts an end to any immediate chance of regaining the top ranking from Andy Murray.
The pair gave notice of a marathon with a 16-minute opening game, with the first four sets going for more than four hours.
Djokovic, who has not quite been himself since winning the French Open last spring to complete his career Grand Slam title sweep, dropped the first set in a tiebreaker but won the next two.
But Istomin had other plans. After levelling at two apiece, Istomin got up a break in the fifth and never looked back.
"It is the biggest win for me. It means so much," Istomin said.
"It's a tennis match," Djokovic said. "On a given day, you can lose. Nothing is impossible."
There were wins for an ailing Milos Raonic, 6-3, 6-4, 7-6 (7-4) over Gilles Muller, and French sixth seed Gael Monfils who beat Alexandr Dolgopolov 6-3, 6-4, 1-6, 6-0.
Ninth seed Rafael Nadal ousted former finalist Marcos Baghdatis 6-3, 6-1, 6-3, and Belgian No. 11 David Goffin rolled past veteran qualifier Radek Stepanek 6-0, 6-4, 6-3.
Two more Frenchman advanced as Gilles Simon dispatched Rogerio Dutra Silva 6-4, 6-1, 6-1 and Richard Gasquet routed Carlos Berlocq 6-1, 6-1, 6-1.
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On the women's side, Mirjana Lucic-Baroni, 34, who last won a Melbourne match in 1998, shocked third seed Agnieszka Radwanska 6-3, 6-2 in less than an hour while second seed Serena Williams overcame Lucie Safarova 6-3, 6-4.
U.S. Open finalist and fifth seed Karolina Pliskova cruised by Russian Anna Blinkov 6-0, 6-2 while sixth seed Dominika Cibulkova put out Hsieh Su-Wei 6-4, 7-6 (10-8). British ninth seed Johanna Konta beat Naomi Osaka 6-4, 6-2.
Pliskova took less than an hour and did not let her opponent into the match until the fifth game.
"I'm feeling pretty good on the court, confident," Pliskova said. "Even if the opponents were not that high level, I felt pretty good out there."
Former world No. 1 Caroline Wozniacki credited a new personal physiotherapist with helping her romp over Donna Vekic 6-1, 6-3, as she moved into the third round.
Wozniacki spent several months of last season out of the sport with an ankle injury and other injuries. She has now won 27 of her last 32 matches.
"I have a full-time physio with me all the time, which has really helped me," the player who topped the rankings in 2010 said. "I get treatment every day, just to keep on top of my body and help me recover, and it's really helped me a lot."