Stadium: Center Court Round: 26 Ground: Clay
| ITF W25 - Santa Margherita | 2022/10/14 12:30 | Deborah Chiesa v Matilde Paoletti | 6-4,3-6,3-6 |
| ITF W60 - Rome | 2023/07/11 12:45 | Nuria Brancaccio v Matilde Paoletti | 2-6,6-2,3-6 |
| WTA Florence | 2023/05/19 15:50 | Matilde Paoletti v Taylor Townsend | 3-6,2-6 |
| WTA Florence | 2023/05/18 13:40 | Matilde Paoletti v Nuria Brancaccio | 2-6,7-6,6-4 |
| WTA Florence | 2023/05/17 11:30 | Jule Niemeier v Matilde Paoletti | 3-6,6-3,3-6 |
| WTA Rom | 2023/05/10 10:30 | Matilde Paoletti v Magdalena Frech | 6-4,2-6,5-7 |
| ITF W25 - Santa Margherita | 2023/04/20 11:00 | Ekaterina Makarova v Matilde Paoletti | 6-4,6-2 |
| ITF W25 - Santa Margherita | 2023/04/19 10:45 | Matilde Paoletti v Malene Helgo | 6-4,7-5 |
| ITF W25 - Santa Margherita | 2023/04/13 08:30 | Matilde Paoletti v Sofia Costoulas | 1-6,3-6 |
| ITF W60 - Rome | 2023/07/12 09:05 | Deborah Chiesa v Anastasia Abbagnato | 6-1,6-2 |
| ITF W60 - Rome | 2023/07/11 10:40 | Deborah Chiesa v Eleonora Alvisi | 6-4,6-3 |
| ITF W60 - Caserta | 2023/06/07 09:35 | Louisa Chirico v Deborah Chiesa | 6-4,6-3 |
| ITF W60 - Brescia | 2023/05/31 09:35 | Deborah Chiesa v Lucie Havlickova | 3-6,6-4,4-6 |
| ITF W60 - Brescia | 2023/05/30 07:00 | Gabriela Ce v Deborah Chiesa | 5-7,3-6 |
| ITF W60 - Brescia | 2023/05/29 06:55 | Quinn Gleason v Deborah Chiesa | 1-6,1-6 |
| WTA Florence | 2023/05/16 14:55 | Deborah Chiesa v Ana Bogdan | 2-6,1-6 |
| WTA Florence | 2023/05/15 12:00 | Beatrice Ricci v Deborah Chiesa | 3-6,1-6 |