Stadium: Clay 2 Round: 62 Ground: Clay
| ITF W25 Heraklion | 2023/10/22 11:00 | Leticia Matuszewski v Jessica Bertoldo | 3-6,4-6 |
| ITF W15 Heraklion | 2023/10/18 10:15 | Michaela Laki v Jessica Bertoldo | 6-2,4-6,6-4 |
| ITF W25 Trieste | 2023/08/28 09:15 | Anne Schaefer v Jessica Bertoldo | 6-0,6-2 |
| ITF W25 Trieste | 2023/08/27 14:00 | Jessica Bertoldo v Giorgia Pinto | 6-4,7-6 |
| ITF W15 Vejle | 2023/07/28 09:40 | Jessica Bertoldo v Rebecca Munk Mortensen | 7-6,1-6,2-6 |
| ITF W15 Vejle | 2023/07/27 12:00 | Gaia Squarcialupi v Jessica Bertoldo | 2-6,3-6 |
| ITF W15 Vejle | 2023/07/25 11:55 | Irene Lavino v Jessica Bertoldo | 3-6,7-5,3-6 |
| ITF W15 Kranjska Gora | 2023/06/14 12:15 | Katerina Tsygourova v Jessica Bertoldo | 6-3,6-1 |
| ITF W25 Heraklion | 2023/10/22 11:00 | Karolina Krajmer v Milana Zhabrailova | 2-6,4-6 |
| ITF W15 Heraklion | 2023/10/20 06:55 | Rositsa Dencheva v Milana Zhabrailova | 4-6,6-2,6-2 |
| ITF W15 Heraklion | 2023/10/19 09:05 | Milana Zhabrailova v Ani Vangelova | 6-4,6-0 |
| ITF W15 Heraklion | 2023/10/18 06:25 | Milana Zhabrailova v Gaia Squarcialupi | 4-6,7-5,6-2 |
| ITF W15 Bad Waltersdorf | 2023/10/03 11:45 | Milana Zhabrailova v Timea Jaruskova | 1-6,6-1,4-6 |
| ITF W25 Monastir | 2023/01/24 08:30 | Milana Zhabrailova v Nana Kawagishi | 1-6,6-7 |
| ITF W25 Monastir | 2023/01/23 12:55 | Milana Zhabrailova v Sarah Hawkshaw | 6-3,6-1 |
| ITF W40 Monastir | 2023/01/18 10:30 | Milana Zhabrailova v Iryna Shymanovich | 4-6,7-6,2-6 |