[44] Kaia Kanepi 0-6,6-4,3-6 Serena Williams [26] 2018-09-02 19:45
Stadium: Arthur Ashe Stadium Round: 26 Ground: Hardcourt outdoor
Home History
| US Open Women | 2018/08/31 20:50 | Kaia Kanepi v Rebecca Peterson | 6-3,7-6 |
| US Open Women | 2018/08/29 20:45 | Kaia Kanepi v Jil Teichmann | 6-4,6-3 |
| US Open Women | 2018/08/27 15:00 | Simona Halep v Kaia Kanepi | 2-6,4-6 |
| WTA Cincinnati | 2018/08/15 16:55 | Kaia Kanepi v Ashleigh Barty | 5-7,3-6 |
| WTA Cincinnati | 2018/08/14 17:15 | Kaia Kanepi v Varvara Lepchenko | 2-6,6-3,6-1 |
| WTA Cincinnati Qual | 2018/08/12 14:00 | Kaia Kanepi v Zarina Diyas | 6-3,6-3 |
| WTA Cincinnati Qual | 2018/08/11 17:00 | Kaia Kanepi v Sabine Lisicki | 4-6,6-4,6-3 |
| WTA Moscow | 2018/07/25 08:00 | Olga Danilovic v Kaia Kanepi | 7-6,7-5 |
Away History
| US Open Women | 2018/09/01 00:00 | Serena Williams v Venus Williams | 6-1,6-2 |
| US Open Women | 2018/08/29 23:05 | Serena Williams v Carina Witthoeft | 6-2,6-2 |
| US Open Women | 2018/08/28 00:00 | Serena Williams v Magda Linette | 6-4,6-0 |
| WTA Cincinnati | 2018/08/15 00:30 | Petra Kvitova v Serena Williams | 6-3,2-6,6-3 |
| WTA Cincinnati | 2018/08/13 23:00 | Daria Saville v Serena Williams | 1-6,2-6 |
| WTA San Jose | 2018/08/01 02:00 | Serena Williams v Johanna Konta | 1-6,0-6 |
| Wimbledon Women | 2018/07/14 15:10 | Angelique Kerber v Serena Williams | 6-3,6-3 |
| Wimbledon Women | 2018/07/12 13:25 | Julia Goerges v Serena Williams | 2-6,4-6 |