Australian Open 2019 scores, results: Serena Williams beats top-seeded Simona Halep; Roger Federer knocked out

A handful of big names have advanced at the 2019 Australian Open, but two of the biggest ones have been knocked out. The Open is inching closer to finals territory with the Round of 16 in the books and quarterfinal matches set for the coming days. While major favorites like Naomi Osaka and Novak Djokovic are still alive, Melbourne saw Roger Federer and Simona Halep depart on back-to-back days, marking the loss of both the Women's Tennis Association's No. 1 and the two-time defending men's champion.

Djokovic had little trouble with No. 15 Daniil Medvedev. Ditto for No. 2 Rafael Nadal with Tomas Berdych. But Federer, the oldest man left in the field, saw his hopes of a third straight Australian Open title go down the drain after failing to convert any of his 12 break-point opportunities against No. 14 Stefanos Tsitsipas, who's advanced to take on No. 22 Roberto Bautista Agut at Rod Laver Arena. The 20-year-old Tsitsipas became the first player from Greece to reach a major quarterfinal, but perhaps even more prominently, he becomes the first player to knock out the 37-year-old Federer in Melbourne since 2016.

Halep, meanwhile, entered her anticipated match with No. 16 Serena Williams, the reigning US Open runner-up and seven-time Australian Open champ, in full acknowledgment that her No. 1 seeding didn't necessarily equate to Williams' lifelong resume. And despite strong play on her end, the reigning French Open champion ended up proving herself right, falling to Serena after Williams saved three break points to hold for 3-all in their match's third set. With Halep knocked out, Williams is still positioned to pursue her 24th Grand Slam title, which would tie an all-time record.

Here's a complete rundown of all Round of 16 results, compiled from our breakdown of the entire 2019 Australian Open field:

Men's singles

  • No. 1 Novak Djokovic defeats No. 15 Daniil Medvedev 6-4, 6-7, 6-2, 6-3
  • No. 14 Stefanos Tsitsipas defeats No. 3 Roger Federer 6-7, 7-6, 7-5, 7-6
  • No. 2 Rafael Nadal defeats Tomas Berdych 6-0, 6-1, 7-6
  • No. 16 Milos Raonic defeats No. 4 Alexander Zverev 6-1, 6-1, 7-6
  • No. 28 Lucas Pouille defeats No. 11 Borna Coric 6-7, 6-4, 7-5, 7-6
  • No. 22 Roberto Bautista Agut defeats No. 6 Marin Cilic 6-7, 6-3, 6-2, 4-6, 6-4
  • No. 8 Kei Nishikori defeats No. 23 Pablo Carreno Busta 6-7, 4-6, 7-6, 6-4, 7-6

Women's singles

  • No. 16 Serena Williams defeats No. 1 Simona Halep 6-1, 4-6, 6-4
  • Danielle Rose Collins defeats No. 2 Angelique Kerber 6-0, 6-2
  • Anastasia Pavlyuchenkova defeats No. 5 Sloane Stephens 6-7, 6-3, 6-3
  • No. 4 Naomi Osaka defeats No. 13 Anastasija Sevastova 4-6, 6-3, 6-4
  • No. 6 Elina Svitolina defeats No. 17 Madison Keys 6-1, 1-6, 6-1
  • No. 15 Ashleigh Barty defeats No. 30 Maria Sharapova 4-6, 6-1, 6-4
  • No. 8 Petra Kvitova defeats Amanda Anisimova 6-2, 6-1
  • No. 7 Karolina Pliskova defeats No. 18 Garbine Muguruza 6-3, 6-1
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