[16] Anett Kontaveit 3-6,2-6 Maria Sakkari [39] 2019-05-16 12:55
Stadium: Court 6 Round: 25 Ground: Clay
Head to Head
| WTA Cincinnati | 2018/08/15 19:30 | Maria Sakkari v Anett Kontaveit | 1-6,3-6 |
| WTA Miami | 2018/03/23 18:15 | Anett Kontaveit v Maria Sakkari | 4-6,1-6 |
| Australian Open 2017 Women | 2017/01/17 02:55 | Maria Sakkari v Anett Kontaveit | 6-0,6-4 |
Home History
| WTA Rome | 2019/05/13 15:15 | Anett Kontaveit v Mona Barthel | 4-6,6-4,6-4 |
| WTA Madrid | 2019/05/04 14:40 | Aliaksandra Sasnovich v Anett Kontaveit | 0-6,6-3,6-2 |
| WTA Stuttgart | 2019/04/28 14:00 | Anett Kontaveit v Petra Kvitova | 3-6,6-7 |
| WTA Stuttgart | 2019/04/25 13:05 | Anastasia Pavlyuchenkova v Anett Kontaveit | 3-6,2-6 |
| WTA Stuttgart | 2019/04/24 13:35 | Caroline Garcia v Anett Kontaveit | 4-6,3-6 |
| WTA Miami | 2019/03/28 17:00 | Anett Kontaveit v Ashleigh Barty | 3-6,3-6 |
| WTA Miami | 2019/03/26 18:00 | Su-Wei Hsieh v Anett Kontaveit | 6-3,2-6,5-7 |
| WTA Miami | 2019/03/24 00:40 | Ajla Tomljanovic v Anett Kontaveit | 6-7,6-2,6-7 |
Away History
| WTA Rome | 2019/05/14 09:00 | Maria Sakkari v Anastasia Pavlyuchenkova | 6-1,7-5 |
| WTA Rome | 2019/05/12 14:40 | Maria Sakkari v Andrea Petkovic | 6-2,7-5 |
| WTA Rome | 2019/05/11 14:45 | Maria Sakkari v Vera Zvonareva | 6-4,6-2 |
| WTA Madrid | 2019/05/05 14:55 | Maria Sakkari v Carla Suarez Navarro | 3-6,3-6 |
| WTA Rabat | 2019/05/04 14:00 | Maria Sakkari v Johanna Konta | 2-6,6-4,6-1 |
| WTA Rabat | 2019/05/03 14:45 | Maria Sakkari v Alison Van Uytvanck | 6-4,6-4 |
| WTA Rabat | 2019/05/02 16:15 | Elise Mertens v Maria Sakkari | 4-6,6-7 |
| WTA Rabat | 2019/05/01 12:15 | Isabella Shinikova v Maria Sakkari | 4-6,4-6 |
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