| WTA Moscow Qual | 07/22 07:00 | 45 | [206] Jessica Pieri v Valentini Grammatikopoulou [179] | 2-6,4-6 | |
| WTA Gstaad Qual | 07/15 09:00 | 64 | [145] Veronika Kudermetova v Jessica Pieri [216] | 6-7,6-1,6-2 | |
| WTA Gstaad Qual | 07/14 09:50 | 45 | Diana Maria Mihail v Jessica Pieri | 0-6,1-6 | |
| ITF Women Versmold | 07/12 12:50 | 26 | [216] Jessica Pieri v Olga Danilovic [246] | 1-6,1-6 | |
| ITF Women Versmold | 07/10 13:00 | 25 | [242] Ipek Soylu v Jessica Pieri [216] | 2-6,4-6 | |
| ITF Women Rome | 07/06 11:00 | 27 | [198] Silvia Soler-Espinosa v Jessica Pieri [216] | 7-5,5-7,7-6 | |
| ITF Women Rome | 07/05 10:00 | 26 | [216] Jessica Pieri v Anastasia Grymalska [228] | 6-2,6-3 | |
| ITF Women Rome | 07/04 08:00 | 25 | [216] Jessica Pieri v Chantal Skamlova [274] | 6-1,6-2 | |
| Wimbledon Women Qual | 06/27 10:00 | 45 | [113] Caroline Dolehide v Jessica Pieri [214] | 6-2,6-3 | |
| Wimbledon Women Qual | 06/26 10:00 | 44 | [214] Jessica Pieri v Patty Schnyder [154] | 6-2,6-3 | |
| ITF Women Ilkley Qual | 06/17 13:55 | 54 | [210] Jessica Pieri v Maria Sanchez [254] | 1-6,4-6 | |
| ITF Women Brescia | 06/07 16:00 | 26 | [205] Jessica Pieri v Laura Siegemund [358] | 1-6,0-6 | |
| ITF Women Brescia | 06/06 10:55 | 25 | [205] Jessica Pieri v Ganna Poznikhirenko [255] | 6-4,6-4 | |
| WTA Strasbourg Qual | 05/19 09:00 | 64 | [218] Jessica Pieri v Chloe Paquet [261] | Retired | |
| WTA Strasbourg Qual | 05/18 11:55 | 45 | [218] Jessica Pieri v Diana Marcinkevica [280] | 3-6,7-5,6-3 | |
| ITF Women Saint Gaudens | 05/17 10:20 | 26 | [218] Jessica Pieri v Arantxa Rus [108] | 7-6,1-6,0-6 | |
| ITF Women Saint Gaudens | 05/16 11:00 | 25 | [218] Jessica Pieri v Margot Yerolymos [491] | 6-3,6-2 | |
| WTA Lugano Qual | 04/09 12:45 | - | [124] Danka Kovinic v Jessica Pieri [216] | 6-1,6-2 | |
| WTA Lugano Qual | 04/08 09:00 | 45 | [220] Jessica Pieri v Deborah Chiesa [179] | 4-6,6-2,6-4 | |
| ITF Women Santa Margherita | 04/03 18:20 | 25 | [236] Chantal Skamlova v Jessica Pieri [220] | 7-6,2-6,7-5 | |
| ITF Women Santa Margherita | 03/28 18:45 | 25 | [345] Anastasia Grymalska v Jessica Pieri [218] | 6-4,7-6 | |
| ITF Women Zhuhai | 03/07 03:35 | 25 | Jessica Pieri v Maryna Zanevska | Retired | |
| ITF Women Zhuhai Qual | 03/06 02:00 | 54 | Jessica Pieri v Shuo Feng | 6-0,6-1 | |
| ITF Women Zhuhai Qual | 03/05 02:00 | 54 | Jessica Pieri v Qiu Yu Ye | 6-3,6-2 | |
| ITF Women Zhuhai Qual | 03/04 06:00 | 54 | Jessica Pieri v Yuxuan Zhang | 6-3,6-3 | |
| ITF Women Bergamo | 02/12 11:15 | 25 | Jessica Pieri v Martina Colmegna | 6-7,5-7 | |
| ITF Women Grenoble | 02/07 13:15 | 25 | Jessica Pieri v Eleonora Molinaro | 6-4,1-6,3-6 | |
| ITF Women Santa Margherita | 11/01 13:30 | 25 | [343] Polina Leykina v Jessica Pieri [257] | Retired | |
| ITF Women Santa Margherita | 10/29 13:00 | 29 | [282] Julia Grabher v Jessica Pieri [253] | 4-6,1-6 | |
| ITF Women Santa Margherita | 10/28 12:00 | 28 | [253] Jessica Pieri v Sara Cakarevic [498] | 6-3,6-2 |