Stadium: Centre Court Round: 28 Ground: Hardcourt outdoor
| WTA Beijing | 2017/10/07 06:45 | Jelena Ostapenko v Simona Halep | 2-6,4-6 |
| French Open Women | 2017/06/10 13:00 | Jelena Ostapenko v Simona Halep | 4-6,6-4,6-3 |
| WTA Luxembourg | 2021/09/19 13:00 | Jelena Ostapenko v Clara Tauson | 3-6,6-4,4-6 |
| WTA Luxembourg | 2021/09/18 12:00 | Ludmilla Samsonova v Jelena Ostapenko | 1-6,6-7 |
| WTA Luxembourg | 2021/09/17 10:00 | Jelena Ostapenko v Alize Cornet | 7-6,6-2 |
| WTA Luxembourg | 2021/09/16 10:00 | Jelena Ostapenko v Arianne Hartono | 6-2,4-6,6-1 |
| WTA Luxembourg | 2021/09/14 19:40 | Jelena Ostapenko v Jule Niemeier | 6-2,6-2 |
| WTA Cincinnati | 2021/08/19 16:05 | Angelique Kerber v Jelena Ostapenko | 4-6,6-2,7-5 |
| WTA Cincinnati | 2021/08/16 18:50 | Jelena Ostapenko v Tamara Zidansek | 7-5,6-1 |
| WTA Montreal | 2021/08/09 15:00 | Jelena Ostapenko v Katerina Siniakova | 1-6,3-6 |
| US Open Women | 2021/09/05 16:00 | Elina Svitolina v Simona Halep | 6-3,6-3 |
| US Open Women | 2021/09/03 15:00 | Elena Rybakina v Simona Halep | 6-7,6-4,3-6 |
| US Open Women | 2021/09/01 16:00 | Kristina Kucova v Simona Halep | 3-6,1-6 |
| US Open Women | 2021/08/30 15:00 | Camila Giorgi v Simona Halep | 4-6,6-7 |
| WTA Cincinnati | 2021/08/17 15:00 | Magda Linette v Simona Halep | 4-6,6-3,1-6 |
| WTA Montreal | 2021/08/11 23:00 | Simona Halep v Danielle Rose Collins | 6-2,4-6,4-6 |
| WTA Madrid | 2021/05/04 11:35 | Elise Mertens v Simona Halep | 4-6,7-5,7-5 |
| WTA Madrid | 2021/05/02 14:05 | Saisai Zheng v Simona Halep | 0-6,4-6 |