| ITF - Santa Margherita W25 | 09/19 16:45 | 26 | [471] Julyette M J Steur v Jessica Pieri [350] | 0-6,4-6 | |
| ITF - Santa Margherita W25 | 09/18 12:00 | 25 | [434] Julia Payola v Jessica Pieri [350] | 4-6,2-6 | |
| ITF - Santa Margherita W25 | 09/13 16:00 | 27 | [349] Jessica Pieri v Elisabetta Cocciaretto [417] | 4-6,0-6 | |
| ITF - Santa Margherita W25 | 09/13 12:30 | 26 | Jessica Pieri v Melania Delai | 7-6,6-0 | |
| ITF - Santa Margherita W25 | 09/12 16:35 | 25 | Jessica Pieri v Fernanda Contreras Gomez | 6-3,7-5 | |
| ITF - Trieste W25 | 09/05 08:15 | 26 | [319] Jessica Pieri v Lucrezia Stefanini [472] | Retired | |
| ITF - Trieste W25 | 09/04 09:35 | 25 | [319] Jessica Pieri v Claudia Giovine [406] | 6-7,6-2,6-1 | |
| ITF W25 Bagnatica | 08/28 08:00 | 25 | [319] Jessica Pieri v Tatiana Pieri [375] | Retired | |
| ITF - Braunschweig W25 | 08/22 09:30 | 26 | Anna Klasen v Jessica Pieri | 1-6,6-3,6-0 | |
| ITF - Braunschweig W25 | 08/20 11:45 | 25 | [349] Margot Yerolymos v Jessica Pieri [319] | 5-7,4-6 | |
| ITF W25 Cordenons | 08/09 11:30 | 27 | Nika Radisic v Jessica Pieri | 1-6,6-3,6-4 | |
| ITF W25 Cordenons | 08/08 12:45 | 26 | [392] Melanie Klaffner v Jessica Pieri [341] | 3-6,1-6 | |
| ITF W25 Cordenons | 08/07 12:25 | 25 | Nuria Brancaccio v Jessica Pieri | 2-6,4-6 | |
| ITF W25 Sezze | 08/03 10:30 | 28 | [375] Anna Danilina v Jessica Pieri [329] | 6-4,2-6,6-1 | |
| ITF W25 Sezze | 08/02 12:50 | 27 | [329] Jessica Pieri v Victoria Kan [389] | 7-5,7-5 | |
| ITF W25 Sezze | 08/01 10:50 | 26 | [329] Jessica Pieri v Ekaterina Yashina [416] | 6-2,6-1 | |
| ITF W25 Sezze | 07/31 08:30 | 25 | [329] Jessica Pieri v Oana Georgeta Simion [401] | 1-6,6-2,7-5 | |
| WTA Palermo | 07/22 19:35 | 25 | [354] Jessica Pieri v Aleksandra Krunic [103] | 2-6,3-6 | |
| WTA Palermo | 07/21 18:00 | 64 | [151] Laura Pigossi v Jessica Pieri [340] | 6-4,1-6,0-6 | |
| WTA Palermo | 07/20 20:45 | 45 | [340] Jessica Pieri v Daniela Seguel [254] | 6-4,6-4 | |
| ITF W80 Biarritz | 07/16 09:00 | 25 | [340] Jessica Pieri v Anastasia Zarycka [229] | 0-6,2-6 | |
| ITF - Torino W25 | 07/10 11:05 | 25 | [290] Jessica Pieri v Angelica Moratelli [380] | 2-6,2-6 | |
| ITF W25 Biella | 07/04 12:25 | 26 | [290] Jessica Pieri v Maiar Sherif [500] | 4-6,6-7 | |
| ITF W25 Biella | 07/03 11:00 | 25 | [290] Jessica Pieri v Camilla Rosatello [264] | 6-3,4-6,6-2 | |
| ITF W25 Montpellier | 06/19 08:30 | 25 | [288] Jessica Pieri v Amandine Hesse [230] | 3-6,6-3,4-6 | |
| ITF - Rzym W60 | 06/14 10:50 | 27 | [300] Jessica Pieri v Varvara Flink [152] | 2-6,3-6 | |
| ITF - Rzym W60 | 06/13 13:55 | 26 | [300] Jessica Pieri v Lara Salden [419] | 6-4,6-3 | |
| ITF - Rzym W60 | 06/12 18:30 | 25 | [100] Stefanie Voegele v Jessica Pieri [300] | 4-6,2-6 | |
| ITF - Brescia W60 | 06/05 15:00 | 25 | [186] Martina Di Giuseppe v Jessica Pieri [296] | 7-6,6-2 | |
| ITF - Grado W25 | 05/30 13:40 | 25 | [296] Jessica Pieri v Ashley Kratzer [261] | 5-7,1-6 |