Stadium: Court 3 Round: 26 Ground: Clay
| WTA Lugano Qual | 2018/04/08 09:00 | Jessica Pieri v Deborah Chiesa | 4-6,6-2,6-4 |
| ITF Women Santa Margherita | 2017/09/17 13:00 | Deborah Chiesa v Jessica Pieri | 7-6,6-3 |
| ITF W25 Santa Margherita | 2023/09/20 10:20 | Giorgia Pinto v Deborah Chiesa | 0-6,2-6 |
| ITF W60 Montreux | 2023/09/06 08:00 | Deborah Chiesa v Matilde Jorge | 6-4,1-6,3-6 |
| ITF W60 Montreux | 2023/09/05 11:55 | Jenny Duerst v Deborah Chiesa | 3-6,3-6 |
| ITF W60 Montreux | 2023/09/04 14:45 | Sandy Marti v Deborah Chiesa | 4-6,3-6 |
| ITF W25 Trieste | 2023/08/29 08:55 | Deborah Chiesa v Sofia Rocchetti | 4-6,6-4,4-6 |
| ITF W25 Trieste | 2023/08/28 10:20 | Deborah Chiesa v Katerina Tsygourova | 7-5,6-2 |
| ITF W25 Trieste | 2023/08/27 08:00 | Deborah Chiesa v Maja Radisic | 6-1,6-1 |
| ITF W25 Verbier | 2023/08/23 10:45 | Deborah Chiesa v Dalila Spiteri | 4-6,4-6 |
| ITF W25 Santa Margherita | 2023/09/19 10:55 | Jessica Pieri v Seone Mendez | 6-4,6-1 |
| ITF W40 Saint Palais Sur Mer | 2023/09/06 15:35 | Amandine Hesse v Jessica Pieri | 7-6,6-3 |
| ITF W40 Saint Palais Sur Mer | 2023/09/04 10:00 | Jessica Pieri v Astrid Cirotte | 6-2,6-3 |
| ITF W60 Collonge-Bellerive | 2023/08/30 12:10 | Alina Granwehr v Jessica Pieri | 6-2,2-6,7-5 |
| ITF W60 Collonge-Bellerive | 2023/08/29 14:35 | Jessica Pieri v Estelle Cascino | 6-3,6-0 |
| ITF W60 Collonge-Bellerive | 2023/08/29 09:30 | Jessica Pieri v Marie Mettraux | 6-1,6-1 |
| ITF W25 Bistrita | 2023/08/17 13:05 | Sofia Costoulas v Jessica Pieri | 7-6,6-4 |
| ITF W25 Bistrita | 2023/08/16 07:00 | Jessica Pieri v Eva Maria Ionescu | 6-4,6-2 |