[33] Maria Sakkari 5-7,3-6 Jennifer Brady [80] 2019-06-14 17:45
Stadium: Indoor 4 Round: 27 Ground: Grass
Home History
| WTA Nottingham | 2019/06/13 15:40 | Maria Sakkari v Ivana Jorovic | 6-2,6-4 |
| WTA Nottingham | 2019/06/12 14:30 | Maria Sakkari v Heather Watson | 6-4,6-3 |
| French Open Women | 2019/05/30 09:00 | Katerina Siniakova v Maria Sakkari | 7-6,6-7,6-3 |
| French Open Women | 2019/05/28 16:45 | Anna Tatishvili v Maria Sakkari | 0-6,1-6 |
| WTA Rome | 2019/05/18 15:25 | Karolina Pliskova v Maria Sakkari | 6-4,6-4 |
| WTA Rome | 2019/05/17 17:30 | Kristina Mladenovic v Maria Sakkari | 7-5,3-6,0-6 |
| WTA Rome | 2019/05/16 12:55 | Anett Kontaveit v Maria Sakkari | 3-6,2-6 |
| WTA Rome | 2019/05/14 09:00 | Maria Sakkari v Anastasia Pavlyuchenkova | 6-1,7-5 |
Away History
| WTA Nottingham | 2019/06/13 16:00 | Sara Sorribes Tormo v Jennifer Brady | 4-6,6-3,5-7 |
| WTA Nottingham | 2019/06/12 18:15 | Jennifer Brady v Shuai Zhang | 7-5,6-3 |
| ITF W100 Surbiton | 2019/06/05 11:30 | Caty McNally v Jennifer Brady | 6-4,6-3 |
| French Open Women | 2019/05/29 09:00 | Jennifer Brady v Polona Hercog | 3-6,7-6,4-6 |
| French Open Women | 2019/05/26 17:00 | Jennifer Brady v Ivana Jorovic | 7-6,4-6,7-5 |
| WTA Strasbourg | 2019/05/19 14:35 | Jennifer Brady v Qiang Wang | 4-6,3-6 |
| WTA Madrid | 2019/05/04 11:40 | Margarita Betova v Jennifer Brady | 6-4,7-6 |
| WTA Madrid | 2019/05/03 15:25 | Jennifer Brady v Veronika Kudermetova | 7-6,7-6 |