Third-seeded Marin Cilic recorded his 500th career ATP Tour-level victory on Thursday with a 6-1, 7-6 (5) win over Croatian countryman Ivo Karlovic in the second round of the VTB Kremlin Cup in Moscow.
Cilic, who won this tournament in 2014 and 2015, became the 10th active player and 50th all-time to reach the milestone after dispatching Karlovic in one hour, 23 minutes. He advances to face Frenchman Jeremy Chardy, who posted a 6-3, 6-4 victory over eighth-seeded Miomir Kecmanovic of Serbia.
Sixth-seeded Andrey Rublev of Russia notched a 7-6 (3), 6-7 (8), 6-2 win over Egor Gerasimov of Belarus.
European Open
Eighteen-year-old Italian Jannik Sinner saved the lone break point he faced and stunned top-seeded Frenchman Gael Monfils, 6-3, 6-2, in their second-round match in Antwerp, Belgium.
France's Ugo Humbert posted a 6-3, 6-1 win over second-seeded David Goffin of Belgium, and Romania's Marius Copil bounced third-seeded Argentine Diego Schwartzman, 6-4, 5-7, 7-6 (7) to continue the round of upsets.
Frances Tiafoe posted a 6-3, 6-4 victory over seventh-seeded German Jan-Lennard Struff, and Great Britain's Andy Murray upended eighth-seeded Uruguayan Pablo Cuevas, 6-4, 6-3.
Intrum Stockholm Open
Janko Tipsarevic broke six serves and breezed to a 6-1, 6-1 win over top-seeded Italian Fabio Fognini in their second-round match in Stockholm, Sweden.
Fourth-seeded Canadian Denis Shapovalov recorded a 6-4, 7-6 (3) victory over fellow 20-year-old Alexei Popyrin of Australia.
Fifth-seeded Spaniard Pablo Carreno-Busta advanced with a 6-3, 7-6 (2) win over Italian Gianluca Mager.
--Field Level Media