Top seed Marco Cecchinato fell at the first hurdle at the Kremlin Cup on Wednesday as he was beaten in straight sets by Adrian Mannarino.
Frenchman Mannarino took just 52 minutes to dispatch Cecchinato from Italy 6-2, 6-3 and secure his place in the quarter-finals.
Next up is Egor Gerasimov after the Belarusian qualifier claimed another big scalp. After upsetting defending champion Damir Dzumhur in the first round, Gerasimov saw off the challenge of Benoit Paire in the second round, winning 6-4, 6-4.
In the bottom half of the draw, the third seed Karen Khachanov flew the Russian flag as he secured a 6-4, 7-5 win over Lukas Rosol.
He will face either fifth seed Nick Kyrgios or Mirza Basic in the quarter-final.
Ricardas Berankis, meanwhile, beat Aljaz Bedene 3-6, 7-6 (7-3), 7-6 (7-5) and he awaits the winner of the Daniil Medvedev-Dusan Lajovic encounter.
Rafa looking at the long term.
Forget them failing, says Forget.
Romanian fearful for future.
Plans awaiting go-ahead.
Fabio Fognini goes under the knife.
Juan Martin del Potro makes change to coaching set-up.
John McEnroe rates Nick Kyrgios quite highly.
Karolina Pliskova unimpressed by complaints.
Greg Rusedski on Roger Federer’s Grand Slam hopes.
Will we see Federer sooner than we thought?