Stadium: Show Court 3 Round: 45 Ground: Clay
| Rome, Singles Qualifying W-ITF-ITA-07A | 2019/05/10 15:30 | Daniela Seguel v Dejana Radanovic | 1-6,6-2,6-4 |
| Rome, Singles Qualifying W-ITF-ITA-07A | 2019/05/09 09:00 | Cristian, Jaqueline Adina v Dejana Radanovic | 2-6,0-6 |
| Rome, Singles Qualifying W-ITF-ITA-07A | 2019/05/07 11:10 | Tena Lukas v Dejana Radanovic | 4-6,5-7 |
| Wiesbaden, Simples W-ITF-GER-03A | 2019/05/03 12:00 | Anna Blinkova v Dejana Radanovic | 6-4,3-6,6-1 |
| Wiesbaden, Simples W-ITF-GER-03A | 2019/05/02 11:25 | Dejana Radanovic v Zaja, Anna | 4-6,6-4,6-2 |
| Wiesbaden, Simples W-ITF-GER-03A | 2019/04/30 12:00 | Dejana Radanovic v Lopatetska, Daria | 6-3,6-3 |
| Chiasso, Singles W-ITF-SUI-01A | 2019/04/24 07:15 | Dejana Radanovic v Lara Salden | 6-0,6-7,0-6 |
| Obidos, Singles Qualifying W-ITF-POR-01A | 2019/04/10 13:00 | Nuria Parrizas-Diaz v Dejana Radanovic | 7-6,7-6 |
| WTA - Rome | 2019/05/11 09:20 | Anastasia Grymalska v Monica Puig | 4-6,2-6 |
| WTA Prague | 2019/04/27 13:25 | Iga Swiatek v Anastasia Grymalska | 6-2,6-0 |
| ITF W25 Santa Margherita | 2019/04/19 12:00 | Anastasia Grymalska v Kathinka Von Deichmann | 6-1,3-6,3-6 |
| ITF W25 Santa Margherita | 2019/04/18 12:00 | Anastasia Grymalska v Lucrezia Stefanini | 6-2,6-3 |
| ITF W25 Santa Margherita | 2019/04/17 17:20 | Anastasia Grymalska v Naiktha Bains | 6-1,6-3 |
| Tunis, Singles W-ITF-TUN-21A | 2019/04/11 10:00 | Diane Parry v Anastasia Grymalska | 6-3,5-7,6-1 |
| Tunis, Singles W-ITF-TUN-21A | 2019/04/10 12:30 | Chiraz Bechri v Anastasia Grymalska | 1-6,1-6 |
| Campinas, Singles Qualifying W-ITF-BRA-03A | 2019/03/28 13:00 | Ekaterine Gorgodze v Anastasia Grymalska | 3-6,6-3,7-6 |