Stadium: Regione Abruzzo Round: 25 Ground: Clay
| ITF W15 L'Aquila | 2021/06/22 07:00 | Anastasia Piangerelli v Gaggini, Valentina | 4-6,6-7 |
| ITF W15 L'Aquila | 2021/06/21 08:00 | Gaggini, Valentina v Valentina Losciale | 6-2,6-4 |
| ITF W15 L'Aquila | 2021/06/20 07:00 | Caruso, Beatrice v Gaggini, Valentina | 4-6,2-6 |
| ITF W25 Grado | 2021/05/30 10:30 | Elena Malygina v Gaggini, Valentina | 6-2,7-6 |
| ITF W25 SM de Montbui | 2021/05/24 09:00 | de Las Heras Armenteras, Claudia v Gaggini, Valentina | 6-2,6-2 |
| ITF W25 SM de Montbui | 2021/05/23 11:00 | Leire De Ezcurra v Gaggini, Valentina | 2-6,3-6 |
| ITF - W15 Monastir | 2021/05/02 14:00 | Aubertin, Sarah Lisa v Gaggini, Valentina | 6-4,0-6,10-3 |
| ITF - W15 Monastir | 2021/04/25 12:30 | Gaggini, Valentina v Karola Patricia Bejenaru | 4-6,6-3,7-10 |
| ITF - W15 Sharm El Sheikh | 2019/11/08 08:00 | Zakarlyuk, Marianna v Anastasia Grymalska | 1-6,6-4,6-4 |
| ITF - W15 Sharm El Sheikh | 2019/11/07 09:40 | Lazareva, Margarita v Anastasia Grymalska | 4-6,1-6 |
| ITF - W15 Sharm El Sheikh | 2019/11/05 09:30 | Krasnova, Daria v Anastasia Grymalska | 4-6,2-6 |
| WTA Palermo | 2019/07/20 19:05 | Anastasia Grymalska v Kathinka Von Deichmann | 5-7,1-6 |
| WTA Bucharest | 2019/07/13 13:45 | Anastasia Grymalska v Isabella Shinikova | 4-6,2-6 |
| ITF W25 Torino | 2019/07/12 11:50 | Claudia Giovine v Anastasia Grymalska | 6-4,6-4 |
| ITF W25 Torino | 2019/07/11 12:00 | Dalila Spiteri v Anastasia Grymalska | 5-7,6-4,1-6 |
| ITF W25 Torino | 2019/07/10 15:10 | Molinaro, Eleonora v Anastasia Grymalska | 1-6,4-6 |