Daniil Medvedev crashed out of ATP/WTA Indian Wells Masters after he lost to Gael Monfils. With the shock defeat, Medvedev also lost his world number one ranking.
Monfils sealed victory in 2hr 6min after converting his sixth match point.
Reigning US Open champion Medvedev had looked to be in control after clinically taking the first set immediately after breaking Monfils for a 5-4 lead.
Monfils broke early for a 3-1 lead in the second set, but Medvedev broke back to level at 3-3.
Monfils earned set point in the eighth game with a brilliant backhand up the line before clinching the second set.
With the next two games going on serve, Medvedev was soon in trouble in the seventh game.
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.