Stadium: Court 1 Round: 27 Ground: Hardcourt outdoor
| French Open Women | 2019/05/31 11:45 | Veronika Kudermetova v Kaia Kanepi | 6-4,3-6,0-6 |
| French Open Women | 2019/05/29 09:00 | Shuai Zhang v Kaia Kanepi | 7-6,0-6,5-7 |
| French Open Women | 2019/05/27 09:00 | Kaia Kanepi v Julia Goerges | 7-5,6-1 |
| WTA Madrid | 2019/05/04 10:55 | Kristyna Pliskova v Kaia Kanepi | 7-6,6-2 |
| WTA Madrid | 2019/05/03 13:25 | Mandy Minella v Kaia Kanepi | 4-6,6-3,2-6 |
| WTA Charleston | 2019/04/04 19:15 | Danielle Rose Collins v Kaia Kanepi | 7-6,6-1 |
| WTA Charleston | 2019/04/03 17:15 | Kaia Kanepi v Elise Mertens | 0-6,6-0,7-5 |
| WTA Charleston | 2019/04/02 18:40 | Veronika Kudermetova v Kaia Kanepi | 6-7,3-6 |
| ITF W25 Grado | 2019/05/30 12:00 | Reka-Luca Jani v Isabella Shinikova | 6-4,3-6,7-5 |
| WTA Rabat | 2019/05/01 12:15 | Isabella Shinikova v Maria Sakkari | 4-6,4-6 |
| WTA Rabat | 2019/04/29 12:40 | Tatjana Maria v Isabella Shinikova | 4-6,2-6 |
| WTA Stuttgart | 2019/04/21 11:30 | Vera Zvonareva v Isabella Shinikova | 6-2,6-1 |
| WTA Stuttgart | 2019/04/20 14:00 | Sabine Lisicki v Isabella Shinikova | 6-3,3-6,6-7 |
| ITF W60 Istanbul | 2019/04/12 11:00 | Jana Cepelova v Isabella Shinikova | 6-4,3-6,6-2 |
| ITF W60 Istanbul | 2019/04/12 07:30 | Ilona Kremen v Isabella Shinikova | 4-6,6-7 |
| ITF W25 Bolton | 2019/04/05 10:35 | Isabella Shinikova v Jodie Anna Burrage | 1-6,0-6 |