Jannik Sinner registered one of the biggest wins of his career, upsetting top-seeded Stefanos Tsitsipas 6-4, 6-3 on Thursday in the second round of the ABN AMRO Open in Rotterdam, Netherlands.

Sinner, a 21-year-old Italian, never previously had defeated a player ranked in the top three in the world. Tsitsipas, a 24-year-old Greek, is rated No. 3 in the world after reaching the Australian Open final.

A dominating serving performance carried Sinner, who won 89 percent of his first-serve points (24 of 27) and never faced a break point.

Also advancing to the quarterfinals were third-seeded Felix Auger-Aliassime of Canada, sixth-seeded Daniil Medvedev of Russia and Alex de Minaur of Australia. The Netherlands’ Gijs Brouwer advanced when fourth-seeded Holger Rune of Denmark retired due a right wrist injury while trailing 6-4, 4-0.

Argentina Open

Spain’s Bernabe Zapata Miralles needed just 77 minutes to rout fourth-seeded Diego Schwartzman of Argentina 6-1, 6-3 in the second round at Buenos Aires.

In a match that featured no aces, Zapata Miralles offset losing all three of the break points on his serve by converting seven of his 14 break opportunities.

Third-seeded Lorenzo Musetti of Italy eliminated Argentina’s Pedro Cachin 6-2, 6-3, and fifth-seeded Francisco Cerundolo of Argentina got past Spain’s Jaume Munar 6-2, 6-1. Peruvian qualifier Juan Pablo Varillas beat Austrian wild-card entrant Dominic Thiem 6-4, 6-4.

Delray Beach Open

The top two seeds both cruised to second-round wins in Delray Beach, Fla.

No. 1 Taylor Fritz of the United States topped Ecuador’s Emilio Gomez 6-4, 6-3 in 87 minutes, and second-seeded Tommy Paul won an all-U.S. matchup against Denis Kudla, 6-3, 6-4.

France’s Adrian Mannarino upset ninth-seeded J.J. Wolf of the United States 7-5, 6-2, and Moldova’s Radu Albot, the 2019 Delray Beach champion, downed Australia’s Aleksandar Vukic 6-4, 6-4.

–Field Level Media