Germany's Alexander Zverev reached the last 16 of the Toronto Masters after claiming his 500th tour-level win on Thursday evening. Zverev defeated Matteo Arnaldi 6-7 (5-7), 6-3, 6-2 to become the ...

The German, who was born in 1997, is the first man born in 1990 or later—or even 1989 or later—to achieve the feat.