Daniil Medvedev crashed out of Indian Wells and lost his world number one ranking after Gael Monfils handed him a 4-6, 6-3, 6-1 shock loss on Monday in the third round.
The Frenchman clinched the win on the sixth match point in front of an adoring California crowd with a backhand winner, letting out a roar as he set up a meeting with Spanish teenager Carlos Alcaraz in the fourth round.
"I'm quite happy right now — I'm in my zone," Monfils said. "I moved quite good and then I changed the speed quite a lot."
Monfils handed Medvedev the break in the ninth game of the first set with a pair of double faults and two forehand errors, as the reigning US Open champion dropped just four points on his serve in the opener.
But Medvedev lost the momentum in the second set, unable to convert on five of six break point opportunities.
Monfils broke him in the fourth game with a backhand winner and again in the eighth with a fiery forehand.
Overcoming obvious exhaustion, Monfils won the first four games of the final set as Medvedev was unable to set up a single break point opportunity.
Medvedev was only able to get 50 per cent of his first serves in, and won only 64 per cent of points on first serve.
Overall, he saved nine break points, but was broken five times.
It was the first time in 13 years that the 35-year-old Monfils beat the number-one ranked player in the world.
In the round of 32, Alcaraz made quick work defeating countryman Roberto Bautista Agut 6-2, 6-0 to advance to meet the Frenchman.
Reuters/ABC