Stadium: Sparta Court A Round: 25 Ground: Hardcourt outdoor
| ITF W100 Ilkley | 2019/06/18 12:15 | Robin Anderson v Valentini Grammatikopoulou | 6-1,6-4 |
| WTA Prague | 2020/09/01 08:00 | Martina Trevisan v Valentini Grammatikopoulou | 2-6,1-6 |
| WTA Prague | 2020/08/30 16:25 | Valentini Grammatikopoulou v Nuria Parrizas-Diaz | 6-4,6-1 |
| ITF W25 Olimpia | 2020/03/11 13:00 | Valentini Grammatikopoulou v Karin Kennel | 2-6,7-6,7-6 |
| ITF W25 Moscow | 2020/02/28 10:45 | Valentini Grammatikopoulou v Taisiya Pachkaleva | 6-7,4-6 |
| ITF W25 Moscow | 2020/02/27 10:40 | Valentini Grammatikopoulou v Vlada Koval | 6-3,6-3 |
| ITF W25 Moscow | 2020/02/26 13:20 | Valentini Grammatikopoulou v Valeriya Strakhova | 3-6,6-3,6-3 |
| ITF W25 Grenoble | 2020/02/12 10:25 | Harmony Tan v Valentini Grammatikopoulou | 5-7,6-1,6-3 |
| 2020 Fed Cup | 2020/02/08 10:55 | Isabella Shinikova v Valentini Grammatikopoulou | 6-3,6-1 |
| WTA Prague | 2020/09/01 08:00 | Robin Anderson v Martina Di Giuseppe | 6-4,6-3 |
| WTA Prague | 2020/08/30 15:00 | Robin Anderson v Dejana Radanovic | 7-6,6-4 |
| WTA Lexington | 2020/08/10 19:15 | Robin Anderson v Bethanie Mattek-Sands | 3-6,6-4,5-7 |
| WTA Lexington | 2020/08/09 21:00 | Ann Li v Robin Anderson | 6-7,5-7 |
| ITF W25 Las Vegas | 2020/03/04 18:00 | Emiliana Arango v Robin Anderson | 6-2,5-7,6-2 |
| ITF W100 Nicholasville | 2020/02/13 18:10 | Gabriela Talaba v Robin Anderson | 6-7,6-4,6-2 |
| ITF W100 Nicholasville | 2020/02/12 20:00 | Robin Anderson v Yuxuan Zhang | 4-6,6-3,6-3 |
| ITF W100 Midland | 2020/02/06 16:55 | Robin Anderson v Jamie Loeb | 3-6,6-4,2-6 |