| ITF W25 Madrid | 06/11 08:35 | 27 | [439] Rebeka Masarova v Jessica Pieri [249] | 5-7,4-6 | |
| ITF W25 Madrid | 06/10 10:35 | 26 | [383] Carole Monnet v Jessica Pieri [249] | 1-6,6-7 | |
| ITF W25 Madrid | 06/09 13:00 | 25 | Nastja Kolar v Jessica Pieri | 6-1,2-6,6-7 | |
| ITF W25 Grado | 06/01 07:00 | 25 | Camilla Rosatello v Jessica Pieri | Cancelled | |
| WTA Strasbourg | 05/22 09:00 | 14 | Evita Ramirez v Jessica Pieri | 3-6,6-4,7-6 | |
| WTA Parma | 05/15 15:00 | 14 | [109] Catherine McNally v Jessica Pieri [263] | 6-2,7-6 | |
| ITF W60 La Bisbal | 05/14 10:15 | 27 | [164] Olga Danilovic v Jessica Pieri [263] | 6-4,6-4 | |
| ITF W60 La Bisbal | 05/13 08:00 | 26 | [158] Kateryna Kozlova v Jessica Pieri [263] | 0-6,6-3,4-6 | |
| ITF W60 La Bisbal | 05/11 08:00 | 25 | [263] Jessica Pieri v Timea Babos [108] | 1-6,6-4,7-5 | |
| ITF W60 La Bisbal | 05/10 08:00 | 54 | [272] Valentina Ivakhnenko v Jessica Pieri [263] | 0-6,2-6 | |
| ITF W60 La Bisbal | 05/09 07:55 | 54 | Leyre R Gormaz v Jessica Pieri | 4-6,4-6 | |
| ITF W60 Zagreb | 05/01 09:00 | 28 | [165] Anhelina Kalinina v Jessica Pieri [287] | 6-2,6-0 | |
| ITF W60 Zagreb | 04/30 09:00 | 27 | [156] Barbara Haas v Jessica Pieri [287] | 2-6,7-5,1-6 | |
| ITF W60 Zagreb | 04/29 08:00 | 26 | [287] Jessica Pieri v Elena Gabriela Ruse [175] | 4-6,7-6,6-3 | |
| ITF W60 Zagreb | 04/28 09:40 | 25 | [287] Jessica Pieri v Martina Di Giuseppe [215] | 2-6,6-2,6-2 | |
| ITF W60 Zagreb | 04/26 09:40 | 54 | [228] Na-Lae Han v Jessica Pieri [287] | 3-6,1-6 | |
| ITF W60 Zagreb | 04/25 10:00 | 54 | [387] Alice Rame v Jessica Pieri [295] | 5-7,2-6 | |
| ITF W25 Calvi | 04/16 13:55 | 27 | [292] Jessica Pieri v Susan Bandecchi [261] | 2-6,2-6 | |
| ITF W25 Calvi | 04/15 12:30 | 26 | Jessica Pieri v Clothilde De Bernardi | 4-6,6-3,6-1 | |
| ITF W25 Calvi | 04/13 14:05 | 25 | Jessica Pieri v Julie Belgraver | 6-2,6-4 | |
| ITF W25 Manacor | 03/06 10:55 | 28 | Jessica Pieri v Nuria Parrizas-Diaz | Walkover | |
| ITF W25 Manacor | 03/05 10:00 | 27 | [296] Jessica Pieri v Jana Fett [210] | 6-3,6-4 | |
| ITF W25 Manacor | 03/04 10:30 | 26 | Iva Primorac v Jessica Pieri | 0-6,2-6 | |
| ITF W25 Manacor | 03/03 11:30 | 25 | Jessica Pieri v Alba C Marin | 2-6,7-5,6-3 | |
| ITF W25 Moszkva | 02/24 11:10 | 25 | [295] Jessica Pieri v Isabella Shinikova [211] | 6-7,7-6,4-6 | |
| ITF W60 Andrezieux-Boutheon | 01/26 09:00 | 54 | Jessica Pieri v Diana Marcinkevica | Retired | |
| ITF W60 Andrezieux-Boutheon | 01/25 09:00 | 54 | [249] Lara Salden v Jessica Pieri [292] | 3-6,4-6 | |
| ITF W25 Hamburg | 01/14 10:00 | 26 | Jessica Pieri v Noma Noha Akugue | 1-6,3-6 | |
| ITF W25 Hamburg | 01/12 16:15 | 25 | Nastasja M Schunk v Jessica Pieri | 7-5,4-6,3-6 | |
| WTA Abu Dhabi | 01/06 06:00 | 19 | [275] Anna Bondar v Jessica Pieri [294] | 4-6,6-4,7-5 |