[77] Jelena Ostapenko 6-4,6-3 Alison Riske [36] 2019-08-29 20:10
Stadium: Grandstand Round: 24 Ground: Hardcourt outdoor
Home History
| US Open Women | 2019/08/27 15:00 | Aleksandra Krunic v Jelena Ostapenko | 3-6,6-7 |
| WTA Cincinnati | 2019/08/12 15:00 | Jelena Ostapenko v Yulia Putintseva | 2-6,7-6,3-6 |
| WTA Toronto | 2019/08/08 23:00 | Marie Bouzkova v Jelena Ostapenko | 6-2,6-2 |
| WTA Toronto | 2019/08/07 19:30 | Jelena Ostapenko v Anastasia Pavlyuchenkova | 6-2,2-6,6-4 |
| WTA Toronto | 2019/08/05 21:00 | Caroline Garcia v Jelena Ostapenko | 3-6,3-6 |
| WTA Jurmala | 2019/07/23 18:45 | Jelena Ostapenko v Bernarda Pera | 2-6,1-6 |
| Wimbledon Women | 2019/07/01 17:15 | Su-Wei Hsieh v Jelena Ostapenko | 6-2,6-2 |
| WTA Eastbourne | 2019/06/25 16:10 | Sloane Stephens v Jelena Ostapenko | 6-1,0-6,3-6 |
Away History
| US Open Women | 2019/08/27 15:00 | Alison Riske-Amritraj v Garbine Muguruza | 2-6,6-1,6-3 |
| WTA Cincinnati | 2019/08/12 23:00 | Maria Sharapova v Alison Riske-Amritraj | 6-3,7-6 |
| WTA Toronto | 2019/08/07 15:00 | Karolina Pliskova v Alison Riske-Amritraj | 6-4,6-7,6-2 |
| WTA Toronto | 2019/08/06 18:50 | Maria Sakkari v Alison Riske-Amritraj | 6-4,2-6,6-7 |
| WTA Toronto | 2019/08/04 14:00 | Alison Riske-Amritraj v Varvara Lepchenko | 6-4,6-4 |
| WTA Toronto | 2019/08/03 14:00 | Alison Riske-Amritraj v Carol Zhao | 6-2,6-1 |
| Wimbledon Women | 2019/07/09 12:00 | Alison Riske-Amritraj v Serena Williams | 4-6,6-4,3-6 |
| Wimbledon Women | 2019/07/08 10:00 | Ashleigh Barty v Alison Riske-Amritraj | 6-3,2-6,3-6 |