[70] Kaia Kanepi 5-7,5-7 Leylah Fernandez [73] 2021-09-01 15:50
Stadium: Court 11 Round: 24 Ground: Hardcourt outdoor
Home History
| US Open Women | 2021/08/30 15:00 | Yulia Putintseva v Kaia Kanepi | 6-2,6-7,2-6 |
| WTA Chicago | 2021/08/24 16:00 | Marta Kostyuk v Kaia Kanepi | 6-2,6-3 |
| WTA Chicago | 2021/08/22 19:50 | Kaia Kanepi v Anhelina Kalinina | 3-6,6-2,7-5 |
| ITF W25 Parnu | 2021/08/08 10:25 | Kaia Kanepi v Anna Siskova | 7-5,6-4 |
| ITF W25 Parnu | 2021/08/07 11:20 | Kaia Kanepi v Berfu Cengiz | 6-1,6-1 |
| ITF W25 Parnu | 2021/08/06 14:00 | Kaia Kanepi v Sinja Kraus | 2-6,7-5,6-2 |
| ITF W25 Parnu | 2021/08/05 12:00 | Kaia Kanepi v Ekaterina Shalimova | 6-1,6-4 |
| ITF W25 Parnu | 2021/08/03 12:00 | Kaia Kanepi v Sarah Beth Grey | 6-0,6-3 |
Away History
| US Open Women | 2021/08/30 15:00 | Leylah Annie Fernandez v Ana Konjuh | 7-6,6-2 |
| WTA Cincinnati | 2021/08/17 02:20 | Alison Riske-Amritraj v Leylah Annie Fernandez | 6-2,6-2 |
| WTA Cincinnati | 2021/08/15 19:00 | Elena-Gabriela Ruse v Leylah Annie Fernandez | 2-6,0-6 |
| WTA Cincinnati | 2021/08/14 19:30 | Irina-Camelia Begu v Leylah Annie Fernandez | 3-6,3-6 |
| WTA Montreal | 2021/08/09 23:00 | Harriet Dart v Leylah Annie Fernandez | 7-5,7-6 |
| Olympics 2020 - Women | 2021/07/26 02:00 | Leylah Annie Fernandez v Barbora Krejcikova | 2-6,4-6 |
| Olympics 2020 - Women | 2021/07/24 02:00 | Leylah Annie Fernandez v Dayana Yastremska | 6-3,3-6,6-0 |
| Wimbledon Women | 2021/06/30 15:50 | Leylah Annie Fernandez v Jelena Ostapenko | 1-6,2-6 |