Stadium: Tillmans Court 7 Versmold Round: 25 Ground: Clay
| ITF W60 Versmold | 2019/07/08 09:00 | Hering, Katharina v Shoshyna, Anastasiya | 7-5,2-6,6-10 |
| Torun, Singles W-ITF-POL-01A | 2019/06/04 09:00 | Carolina Alves v Shoshyna, Anastasiya | 6-1,6-4 |
| Torun, Singles W-ITF-POL-01A | 2019/06/03 08:00 | Husaric, Anita v Shoshyna, Anastasiya | 3-6,1-6 |
| Essen, Simples W-ITF-GER-06A | 2019/05/29 10:00 | Shoshyna, Anastasiya v Elena-Gabriela Ruse | 1-6,6-7 |
| Obidos, Singles Qualifying W-ITF-POR-01A | 2019/04/12 09:30 | Shapatava, Sofia v Shoshyna, Anastasiya | 6-4,6-2 |
| Obidos, Singles Qualifying W-ITF-POR-01A | 2019/04/11 09:00 | Heisen, Vivian v Shoshyna, Anastasiya | 1-6,3-6 |
| Obidos, Singles Qualifying W-ITF-POR-01A | 2019/04/09 15:45 | Shoshyna, Anastasiya v Katy Dunne | 1-6,6-2,6-3 |
| Obidos, Singles Qualifying W-ITF-POR-01A | 2019/04/02 12:50 | Shoshyna, Anastasiya v Pemra Ozgen | 4-6,7-6,1-6 |
| ITF W25 Den Haag | 2019/07/02 10:30 | Valentini Grammatikopoulou v Eva Vedder | 2-6,3-6 |
| Wimbledon Women | 2019/06/25 16:35 | Valentini Grammatikopoulou v Kaja Juvan | 4-6,6-3,8-10 |
| ITF W100 Ilkley | 2019/06/18 12:15 | Robin Anderson v Valentini Grammatikopoulou | 6-1,6-4 |
| ITF W100 Ilkley | 2019/06/17 14:10 | Barnett, Alicia v Valentini Grammatikopoulou | 6-7,6-2,7-10 |
| ITF W60 Rome | 2019/06/13 08:30 | Conny Perrin v Valentini Grammatikopoulou | 6-2,6-2 |
| ITF W60 Rome | 2019/06/11 13:50 | Elisabetta Cocciaretto v Valentini Grammatikopoulou | 4-6,4-6 |
| French Open Women | 2019/05/24 11:15 | Valentini Grammatikopoulou v Varvara Lepchenko | 2-6,2-6 |
| French Open Women | 2019/05/23 09:45 | Heather Watson v Valentini Grammatikopoulou | 5-7,7-6,6-7 |