[10] Serena Williams 6-3,6-4 Naomi Osaka [2] 2019-05-16 03:00
Stadium: Center Court Round: 27 Ground: Hardcourt outdoor
Head to Head
| US Open Women | 2018/09/08 20:00 | Serena Williams v Naomi Osaka | 2-6,4-6 |
| WTA Miami | 2018/03/21 20:35 | Serena Williams v Naomi Osaka | 3-6,2-6 |
Home History
| WTA Rome | 2019/05/13 11:45 | Serena Williams v Rebecca Peterson | 6-4,6-2 |
| WTA Miami | 2019/03/22 20:35 | Rebecca Peterson v Serena Williams | 3-6,6-1,1-6 |
| WTA Indian Wells | 2019/03/09 02:00 | Victoria Azarenka v Serena Williams | 5-7,3-6 |
| Australian Open Women | 2019/01/23 02:00 | Serena Williams v Karolina Pliskova | 4-6,6-4,5-7 |
| Australian Open Women | 2019/01/21 08:00 | Simona Halep v Serena Williams | 1-6,6-4,4-6 |
| Australian Open Women | 2019/01/19 03:25 | Dayana Yastremska v Serena Williams | 2-6,1-6 |
| Australian Open Women | 2019/01/17 09:20 | Eugenie Bouchard v Serena Williams | 2-6,2-6 |
| Australian Open Women | 2019/01/15 01:35 | Tatjana Maria v Serena Williams | 0-6,2-6 |
Away History
| WTA Madrid | 2019/05/09 12:20 | Naomi Osaka v Belinda Bencic | 6-3,2-6,5-7 |
| WTA Madrid | 2019/05/08 11:10 | Naomi Osaka v Aliaksandra Sasnovich | 6-2,6-3 |
| WTA Madrid | 2019/05/07 11:20 | Naomi Osaka v Sara Sorribes Tormo | 7-6,3-6,6-0 |
| WTA Madrid | 2019/05/05 09:00 | Naomi Osaka v Dominika Cibulkova | 6-2,7-6 |
| WTA Stuttgart | 2019/04/26 13:20 | Naomi Osaka v Donna Vekic | 6-3,4-6,7-6 |
| WTA Stuttgart | 2019/04/25 11:30 | Naomi Osaka v Su-Wei Hsieh | 6-4,6-3 |
| WTA Miami | 2019/03/23 18:55 | Naomi Osaka v Su-Wei Hsieh | 6-4,6-7,3-6 |
| WTA Miami | 2019/03/22 16:00 | Naomi Osaka v Yanina Wickmayer | 6-0,6-7,6-1 |