[115] Kaia Kanepi 7-5,6-1 Valentini Grammatikopoulou [232] 2019-09-25 19:20
Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
Home History
| US Open Women | 2019/08/29 21:00 | Kaia Kanepi v Donna Vekic | 5-7,3-6 |
| US Open Women | 2019/08/27 17:45 | Kaia Kanepi v Tatjana Maria | 5-7,7-6,6-3 |
| New York, USA | 2019/08/19 19:25 | Magda Linette v Kaia Kanepi | 6-2,7-5 |
| New York, USA | 2019/08/18 16:15 | Kaia Kanepi v Nadiia Kichenok | 6-7,6-1,6-2 |
| New York, USA | 2019/08/17 16:55 | Kaia Kanepi v Hibi, Mayo | 6-3,6-4 |
| New York, USA | 2019/08/16 19:20 | Kaia Kanepi v Eugenie Bouchard | 6-4,3-6,6-3 |
| WTA Cincinnati | 2019/08/10 15:25 | Srtycova, Barbora v Kaia Kanepi | 7-6,3-6,6-3 |
| Wimbledon Women | 2019/07/04 16:10 | Kaia Kanepi v Bencic, Belinda | 3-6,1-6 |
Away History
| Podgorica, Singles Qualifying W-ITF-MNE-01A | 2019/09/20 09:00 | Amina Anshba v Valentini Grammatikopoulou | 7-5,7-6 |
| Podgorica, Singles Qualifying W-ITF-MNE-01A | 2019/09/19 10:00 | Detiuc, Anastasia v Valentini Grammatikopoulou | 6-4,2-6,6-7 |
| Podgorica, Singles Qualifying W-ITF-MNE-01A | 2019/09/18 11:00 | Nika Radisic v Valentini Grammatikopoulou | 4-6,1-6 |
| ITF W25 Frydek Mistek | 2019/09/11 13:15 | Gerlach, Katharina v Valentini Grammatikopoulou | 6-0,6-2 |
| ITF W25 Trieste | 2019/09/06 09:00 | Lucrezia Stefanini v Valentini Grammatikopoulou | 6-1,6-0 |
| ITF W25 Trieste | 2019/09/05 08:15 | Camilla Rosatello v Valentini Grammatikopoulou | 4-6,5-7 |
| ITF W25 Trieste | 2019/09/04 07:00 | Ponomar, Lisa v Valentini Grammatikopoulou | 2-6,0-6 |
| US Open Women | 2019/08/19 15:00 | Maddison Inglis v Valentini Grammatikopoulou | 6-3,6-4 |