| ITF W40 Macon | 02/20 10:00 | 54 | Jessica Pieri v Jenny Lim | 7-6,6-0 | |
| ITF W40 Macon | 02/19 09:00 | 54 | [312] Sapfo Sakellaridi v Jessica Pieri [494] | 4-6,1-6 | |
| ITF W25 Antalya | 02/05 07:00 | 62 | Jessica Pieri v Ekaterina Perelygina | 6-3,6-2 | |
| ITF W25 Boca Raton | 01/20 15:00 | 27 | Jessica Pieri v Renata Zarazua | 2-6,1-6 | |
| ITF W25 Boca Raton | 01/19 14:30 | 26 | Chiara Scholl v Jessica Pieri | Walkover | |
| ITF W25 Boca Raton | 01/18 15:55 | 25 | Eleana Yu v Jessica Pieri | 6-2,4-6,1-6 | |
| ITF W25 Naples | 01/10 17:30 | 54 | Jessica Pieri v Lauren Proctor | 3-6,6-4,10-12 | |
| ITF W25 Naples | 01/09 17:30 | 54 | Jessica Pieri v Fernanda Naves Anzaldo | 6-0,6-2 | |
| ITF W25 Santa Margherita | 10/13 12:30 | 25 | [447] Jessica Pieri v Misaki Matsuda [335] | 3-6,2-6 | |
| WTA Parma | 09/24 08:50 | 14 | [122] Anna Karolina Schmiedlova v Jessica Pieri [485] | 7-5,6-4 | |
| ITF W25 Santa Margherita | 09/18 12:00 | 29 | [497] Jessica Pieri v Brenda Fruhvirtova [192] | Retired | |
| ITF W25 Santa Margherita | 09/17 11:55 | 28 | [497] Jessica Pieri v Diletta Cherubini [500] | 7-5,6-4 | |
| ITF W25 Santa Margherita | 09/16 12:00 | 27 | [268] Katharina Hobgarski v Jessica Pieri [497] | Retired | |
| ITF W25 Santa Margherita | 09/15 13:35 | 26 | Jessica Pieri v Dalila Spiteri | 6-3,7-6 | |
| ITF W25 Santa Margherita | 09/13 14:20 | 25 | [428] Anna Turati v Jessica Pieri [497] | 6-7,1-6 | |
| ITF W25 Saint Palais Sur Mer | 09/09 15:15 | 27 | [468] Jessica Pieri v Selena Janicijevic [208] | 2-6,6-4,4-6 | |
| ITF W25 Saint Palais Sur Mer | 09/08 12:00 | 26 | [302] Anna Siskova v Jessica Pieri [468] | 3-6,6-7 | |
| ITF W25 Saint Palais Sur Mer | 09/07 11:00 | 25 | Jessica Pieri v Tiantsoa S R Rajaonah | 6-3,7-6 | |
| ITF W25 Trieste | 08/30 13:45 | 25 | [388] Miriam B Bulgaru v Jessica Pieri [468] | 6-0,6-1 | |
| ITF W25 Oldenzaal | 08/26 14:00 | 27 | [473] Jessica Pieri v Magali Kempen [343] | 0-6,6-7 | |
| ITF W25 Oldenzaal | 08/25 16:25 | 26 | [473] Jessica Pieri v Lexie Stevens [490] | 6-1,6-4 | |
| ITF W25 Oldenzaal | 08/23 13:30 | 25 | [381] Matilda Mutavdzic v Jessica Pieri [473] | 7-6,2-6,4-6 | |
| ITF W25 Radom | 08/10 13:45 | 25 | [324] Vera Lapko v Jessica Pieri [468] | 6-1,6-0 | |
| ITF W60 Hechingen | 08/04 15:30 | 26 | [462] Jessica Pieri v Mona Barthel [397] | 2-6,2-6 | |
| ITF W60 Hechingen | 08/03 09:30 | 25 | [462] Jessica Pieri v Arlinda Rushiti [435] | 6-4,2-6,6-1 | |
| ITF W60 Cordenons | 07/27 12:10 | 26 | [106] Panna Udvardy v Jessica Pieri [486] | 6-4,6-0 | |
| ITF W60 Cordenons | 07/25 15:10 | 25 | [311] Lena Papadakis v Jessica Pieri [486] | 4-6,3-6 | |
| ITF W25 Perugia | 07/21 13:55 | 26 | [274] Angela F Boluda v Jessica Pieri [465] | 6-3,6-1 | |
| ITF W25 Perugia | 07/20 14:15 | 25 | Tatiana Pieri v Jessica Pieri | Retired | |
| ITF W25 Getxo | 07/07 09:00 | 26 | [482] Carlota M Cirez v Jessica Pieri [474] | 7-5,6-0 |