Stadium: Court 4 Round: 25 Ground: Clay
| WTA Moscow Qual | 2017/10/15 09:00 | Polina Monova v Valentini Grammatikopoulou | 7-6,6-4 |
| ITF W60 Croissy-Beaubourg | 2019/03/25 17:10 | Cristina Bucsa v Polina Monova | 6-1,6-2 |
| ITF W60 Croissy-Beaubourg | 2019/03/25 12:55 | Alice Robbe v Polina Monova | 6-7,6-3,9-11 |
| ITF W25 Kazan | 2019/03/11 07:00 | Polina Monova v Akgul Amanmuradova | 6-1,7-5 |
| ITF W25 Moscow | 2019/02/27 12:35 | Polina Monova v Maryna Zanevska | 4-6,4-6 |
| ITF W25 Moscow | 2019/02/26 07:00 | Polina Monova v Helene Scholsen | 6-4,3-6,10-6 |
| ITF W25 Moscow | 2019/02/25 10:15 | Polina Monova v Angelina Gabueva | 3-6,7-5,12-10 |
| ITF W25 Kazan | 2019/01/23 08:20 | Valeriya Strakhova v Polina Monova | 2-6,2-6 |
| ITF Women Minsk | 2018/11/09 08:00 | Raluca Georgiana Serban v Polina Monova | 6-4,4-6,6-3 |
| ITF W25 Kofu | 2019/03/20 07:30 | Sandra Samir v Valentini Grammatikopoulou | 1-6,7-5,7-6 |
| ITF W25 Nishi-Tama | 2019/03/14 03:50 | Valentini Grammatikopoulou v Jodie Anna Burrage | 2-6,4-6 |
| ITF W25 Nishi-Tama | 2019/03/13 02:25 | Valentini Grammatikopoulou v Catherine Harrison | 7-5,2-6,7-6 |
| 2019 Fed Cup | 2019/02/08 16:30 | Valentini Grammatikopoulou v Kaja Juvan | 7-6,5-7,6-3 |
| 2019 Fed Cup | 2019/02/07 16:30 | Katie Boulter v Valentini Grammatikopoulou | 6-3,4-6,6-3 |
| 2019 Fed Cup | 2019/02/06 16:30 | Dalma Galfi v Valentini Grammatikopoulou | 6-0,6-3 |
| WTA St. Petersburg | 2019/01/26 18:55 | Valentini Grammatikopoulou v Jana Fett | 1-6,1-6 |
| Australian Open Women | 2019/01/10 06:55 | Bianca Andreescu v Valentini Grammatikopoulou | 6-4,6-1 |