Stadium: Court 12 Round: 54 Ground: Clay
| ITF W15 L'Aquila | 2021/06/23 08:40 | Gaggini, Valentina v Anastasia Grymalska | 2-6,0-6 |
| 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 W25 Torino | 2021/07/06 09:30 | Ylena In-Albon v Enola Chiesa | 6-1,6-2 |
| ITF W25 Torino | 2021/07/05 08:00 | Enola Chiesa v Martina Spigarelli | 6-3,6-4 |
| ITF W15 L'Aquila | 2021/06/21 08:00 | Enola Chiesa v Giulia Carbonaro | 1-6,4-6 |
| ITF W15 L'Aquila | 2021/06/20 07:00 | Enola Chiesa v Miccio, Giuseppina | 6-4,6-0 |
| ITF W15 Sibenik | 2021/05/26 08:00 | Enola Chiesa v Wargnier, Lucie | 3-6,6-2,3-6 |
| ITF W15 Sibenik | 2021/05/25 09:15 | Moravcova, Adela v Enola Chiesa | 2-6,1-6 |
| ITF W15 Sibenik | 2021/05/24 14:10 | Augustinova, Natalie v Enola Chiesa | 2-6,0-6 |
| ITF W15 Sibenik | 2021/05/17 13:55 | Luescher, Sophie v Enola Chiesa | 3-6,6-4,10-8 |