MARSEILLE, France (AP) Top-seeded Milos Raonic of Canada was knocked out of the Open 13 in his first match on Thursday after a shock 6-4, 3-6, 7-6 (3) second-round loss to Simone Bolelli.
It was the Italian's first victory over a top-10 player following 35 defeats.
Raonic, who had a first-round bye, hit 21 aces to Bolelli's seven but converted just one of eight break point opportunities.
Bolelli faces seventh-seeded Gael Monfils of France in the quarterfinals.
Another seeded player, No. 6 David Goffin of Belgium, retired with a rib injury when losing 5-1 to Austria's Dominic Thiem.
The 21-year-old Thiem next plays Roberto Bautista-Agut.
However, fifth-seeded Gilles Simon is safely through after beating Borna Coric 6-2, 3-6, 6-3 to set up a quarterfinal against either Jeremy Chardy or Ernests Gulbis.