| ITF Women Hechingen | 08/09 10:00 | 25 | [240] Tereza Mrdeza v Jessica Pieri [273] | 7-6,4-6,2-6 | |
| ITF Women Bad Saulgau | 08/05 11:00 | 28 | [279] Jessica Pieri v Chiara Scholl [448] | 4-6,7-5,1-6 | |
| ITF Women Bad Saulgau | 08/04 12:20 | 27 | Jessica Pieri v Amina Anshba | 6-4,7-6 | |
| ITF Women Bad Saulgau | 08/03 16:30 | 26 | [132] Tamara Korpatsch v Jessica Pieri [279] | 5-7,6-7 | |
| ITF Women Bad Saulgau | 08/01 13:00 | 25 | Emily Seibold v Jessica Pieri | 1-6,3-6 | |
| ITF Women Horb | 07/26 14:35 | 25 | [269] Jessica Pieri v Julia Wachaczyk [383] | 3-6,3-6 | |
| ITF Women Olomouc | 07/20 10:00 | 26 | [362] Michaela Honcova v Jessica Pieri [278] | 4-6,6-1,6-3 | |
| ITF Women Olomouc | 07/18 08:00 | 25 | [278] Jessica Pieri v Dalila Jakupovic [163] | 7-6,6-3 | |
| ITF Women Torino | 07/12 15:00 | 26 | [297] Jessica Pieri v Alize Lim [266] | 2-6,3-6 | |
| ITF Women Torino | 07/11 13:35 | 25 | Jessica Pieri v Nina Nikprelevic | 6-0,6-0 | |
| ITF Women Rome | 07/08 14:30 | 28 | [297] Jessica Pieri v Kateryna Kozlova [160] | 2-6,4-6 | |
| ITF Women Rome | 07/07 19:20 | 27 | [297] Jessica Pieri v Silvia Soler-Espinosa [154] | 6-1,6-1 | |
| ITF Women Rome | 07/05 18:45 | 26 | [224] Usue Maitane Arconada v Jessica Pieri [297] | 7-5,3-6,1-6 | |
| ITF Women Rome | 07/03 15:30 | 25 | [202] Montserrat Gonzalez v Jessica Pieri [297] | Retired | |
| ITF Women Lenzerheide | 06/21 08:00 | 25 | [281] Jessica Pieri v Elyne Boeykens [381] | 2-6,3-6 | |
| ITF Women Padova | 06/15 19:15 | 26 | [268] Jesika Maleckova v Jessica Pieri [287] | 7-6,6-4 | |
| ITF Women Padova | 06/13 09:00 | 25 | [321] Jaqueline Adina Cristian v Jessica Pieri [287] | 3-6,4-6 | |
| ITF Women Stare Splavy | 06/08 09:00 | 26 | [307] Jessica Pieri v Laura-Ioana Andrei [395] | 2-6,2-6 | |
| ITF Women Stare Splavy | 06/06 09:30 | 25 | Jessica Pieri v Elizabeth Mandlik | 6-1,6-1 | |
| ITF Women Grado | 05/30 13:10 | 25 | Stefania Rubini v Jessica Pieri | 7-6,6-1 | |
| ITF Women Caserta | 05/27 12:30 | 28 | [376] Paula Badosa Gibert v Jessica Pieri [302] | 6-1,6-3 | |
| ITF Women Caserta | 05/26 12:30 | 27 | [302] Jessica Pieri v Andreea Mitu [304] | 7-6,1-6,6-4 | |
| ITF Women Caserta | 05/25 12:45 | 26 | [302] Jessica Pieri v Julia Grabher [286] | 6-1,7-5 | |
| ITF Women Caserta | 05/23 19:30 | 25 | [302] Jessica Pieri v Martina Colmegna [403] | 6-3,6-1 | |
| ITF Women Wiesbaden | 05/03 11:25 | 25 | [302] Jessica Pieri v Anna Karolina Schmiedlova [249] | 7-5,3-6,6-7 | |
| ITF Women Chiasso | 04/20 10:00 | 26 | [257] Sherazad Reix v Jessica Pieri [302] | 6-1,6-7,6-0 | |
| ITF Women Chiasso | 04/18 08:30 | 25 | Simona Waltert v Jessica Pieri | 0-6,3-6 | |
| ITF Women Istanbul | 04/12 08:10 | 26 | [264] Vera Lapko v Jessica Pieri [304] | 6-3,6-4 | |
| ITF Women Istanbul | 04/11 12:25 | 25 | Jessica Pieri v Olga Ianchuk | 6-4,6-4 | |
| ITF Women Santa Margherita | 04/05 12:45 | 25 | [300] Jessica Pieri v Daniela Hantuchova [224] | 7-6,4-6,3-6 |