Daniil Medvedev was the biggest casualty on a day of upsets at the Indian Wells tournament on Monday.
The US Open champion lost 6-4, 3-6, 1-6 to France’s Gael Monfils. The defeat brought an end to his three-week reign as World No 1.
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This was 35-year-old Monfils’ his first win over a World No 1 since 2009. He sealed victory in two hours and six minutes after converting his sixth match point.
“When I play my best tennis, my good tennis, it’s really tough to beat me,” said the Russian. “But that’s the toughest part of tennis is to reproduce it time after time.”
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The shocks continued in the evening session as Greek fifth seed Stefanos Tsitsipas tumbled out to 21-year-old American Jenson Brooksby.
Brooksby, ranked 43rd in the world, advanced to the last 16 with a 1-6, 6-3, 6-2 win.
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Two-time Grand Slam champions Petra Kvitova and Victoria Azarenka were also sent packing.
Maria Sakkari defeated Kvitova 6-3, 6-0 to book a place in the fourth round.
After the tearful exit of four-time Grand Slam champion Naomi Osaka on Saturday, there was another emotional flashpoint as Azarenka succumbed to Kazakh Elena Rybakina 6-3, 6-4.
Rybakina’s victory was overshadowed by a bizarre incident which came while Azarenka prepared to serve while trailing 6-3, 2-2.
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Play was held up for several minutes as the 32-year-old two-time Australian Open champion dissolved into floods of tears, waving away intervention from the chair umpire saying “I’m sorry, I’m really sorry.”
Rybakina described the incident as a “very strange situation”.
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“I just hope everything is good with Vika because I don’t know what happened,” she said. “Hope everything is okay.”