[12] Maria Sakkari 2-6,5-7 Anett Kontaveit [30] 2021-09-26 12:30
Stadium: Centre Court Round: 29 Ground: Hardcourt outdoor
Head to Head
| Olympics 2020 - Women | 2021/07/24 03:30 | Maria Sakkari v Anett Kontaveit | 7-5,6-2 |
| WTA Madrid | 2021/05/02 11:25 | Maria Sakkari v Anett Kontaveit | 6-3,6-1 |
| WTA Grampians Trophy | 2021/02/07 00:30 | Maria Sakkari v Anett Kontaveit | 6-2,3-6,9-11 |
| WTA Rome | 2019/05/16 12:55 | Anett Kontaveit v Maria Sakkari | 3-6,2-6 |
| 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 Ostrava | 2021/09/25 12:00 | Iga Swiatek v Maria Sakkari | 4-6,5-7 |
| WTA Ostrava | 2021/09/24 12:00 | Maria Sakkari v Tereza Martincova | 7-5,6-3 |
| WTA Ostrava | 2021/09/23 11:55 | Maria Sakkari v Jelena Ostapenko | 6-4,6-2 |
| US Open Women | 2021/09/10 02:10 | Emma Raducanu v Maria Sakkari | 6-1,6-4 |
| US Open Women | 2021/09/08 23:00 | Karolina Pliskova v Maria Sakkari | 4-6,4-6 |
| US Open Women | 2021/09/07 02:25 | Maria Sakkari v Bianca Andreescu | 6-7,7-6,6-3 |
| US Open Women | 2021/09/04 16:00 | Petra Kvitova v Maria Sakkari | 4-6,3-6 |
| US Open Women | 2021/09/02 16:00 | Katerina Siniakova v Maria Sakkari | 4-6,2-6 |
Away History
| WTA Ostrava | 2021/09/25 14:10 | Anett Kontaveit v Petra Kvitova | 6-0,6-4 |
| WTA Ostrava | 2021/09/24 17:50 | Anett Kontaveit v Belinda Bencic | 6-4,6-3 |
| WTA Ostrava | 2021/09/22 18:25 | Paula Badosa v Anett Kontaveit | 3-6,4-6 |
| WTA Ostrava | 2021/09/20 16:00 | Sorana Cirstea v Anett Kontaveit | 4-6,4-6 |
| US Open Women | 2021/09/04 19:05 | Anett Kontaveit v Iga Swiatek | 3-6,6-4,3-6 |
| US Open Women | 2021/09/02 16:00 | Anett Kontaveit v Jil Teichmann | 6-4,6-1 |
| US Open Women | 2021/08/31 22:05 | Anett Kontaveit v Samantha Stosur | 6-3,6-0 |
| WTA Cleveland | 2021/08/28 17:00 | Irina-Camelia Begu v Anett Kontaveit | 6-7,4-6 |