Stadium: Court 6 Round: 28 Ground: Hardcourt outdoor
| ITF Women Middelburg | 2017/07/08 10:00 | Dejana Radanovic v Valentini Grammatikopoulou | 6-4,4-6,6-7 |
| ITF Women Monzon | 2017/05/09 11:00 | Dejana Radanovic v Valentini Grammatikopoulou | 7-5,7-6 |
| ITF W25 Kazan | 2020/01/24 07:00 | Dejana Radanovic v Shalimar Talbi | 6-2,6-3 |
| ITF W25 Kazan | 2020/01/23 11:35 | Dejana Radanovic v Berfu Cengiz | 3-6,6-3,6-2 |
| ITF W25 Kazan | 2020/01/22 07:00 | Dejana Radanovic v Darya Astakhova | 6-3,7-6 |
| ITF W100 Shenzhen | 2019/11/04 04:40 | Dejana Radanovic v Nagi Hanatani | 4-6,6-7 |
| ITF W60 Liuzhou | 2019/11/01 03:40 | Dejana Radanovic v Shilin Xu | 2-6,3-6 |
| ITF W60 Liuzhou | 2019/10/31 03:00 | Anastasia Gasanova v Dejana Radanovic | 6-7,4-6 |
| ITF W60 Liuzhou | 2019/10/30 05:45 | Fang Ying Xun v Dejana Radanovic | 7-6,3-6,0-6 |
| ITF W60 Liuzhou | 2019/10/29 02:55 | Dejana Radanovic v Hanyu Guo | 3-6,6-4,6-10 |
| ITF W25 Kazan | 2020/01/24 07:00 | Taisiya Pachkaleva v Valentini Grammatikopoulou | 4-6,6-3,3-6 |
| ITF W25 Kazan | 2020/01/23 07:00 | Vivian Heisen v Valentini Grammatikopoulou | 2-6,1-6 |
| ITF W25 Kazan | 2020/01/21 12:55 | Valeriya Yushchenko v Valentini Grammatikopoulou | 5-7,6-4,5-7 |
| WTA Houston | 2019/11/11 17:15 | Valentini Grammatikopoulou v Eugenie Bouchard | 6-7,4-6 |
| ITF W60 Colina | 2019/11/07 18:15 | Elisabetta Cocciaretto v Valentini Grammatikopoulou | 7-5,6-3 |
| ITF W60 Colina | 2019/11/06 18:00 | Andrea Gamiz v Valentini Grammatikopoulou | 5-7,6-2,5-7 |
| ITF W60 Asuncion | 2019/10/30 19:00 | Valentini Grammatikopoulou v Teliana Pereira | 3-6,2-6 |
| ITF W80 Macon | 2019/10/23 18:30 | Irina Falconi v Valentini Grammatikopoulou | 6-2,6-3 |