| ITF - Hamburg W25 | 01/14 10:00 | 26 | Jessica Pieri v Noma Noha Akugue | 1-6,3-6 | |
| ITF - Hamburg W25 | 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 | |
| WTA Abu Dhabi | 01/05 08:05 | 64 | [366] Katarzyna Piter v Jessica Pieri [294] | 4-6,0-6 | |
| ITF - Porto W25 | 09/27 10:00 | 44 | Jessica Pieri v Ramu Ueda | 5-7,2-6 | |
| WTA Rzym | 09/12 09:35 | 14 | [312] Jessica Pieri v Aliona Bolsova [103] | 1-6,1-6 | |
| WTA Praga | 09/03 09:25 | 26 | [312] Jessica Pieri v Ivana Jorovic [230] | Retired | |
| WTA Praga | 09/02 08:00 | 25 | [148] Leonie Kung v Jessica Pieri [312] | 6-1,1-6,4-6 | |
| WTA Praga | 08/31 08:00 | 25 | [312] Jessica Pieri v Daria Lopatetska [381] | 3-6,7-6,6-4 | |
| WTA Praga | 08/29 12:00 | 24 | [335] Irene Burillo Escorihuela v Jessica Pieri [312] | 4-6,5-7 | |
| Włochy - Umbrian Open - Kobiety | 06/25 08:30 | 1 | Nicole Fossa Huergo v Jessica Pieri | 7-6,6-4 | |
| ITF - Altenkirchen W25 | 02/25 15:00 | 25 | Stefania Rubini v Jessica Pieri | Cancelled | |
| ITF - Grenoble W25 | 02/13 11:15 | 26 | [304] Jessica Pieri v Amandine Hesse [253] | 6-7,6-7 | |
| ITF - Grenoble W25 | 02/11 12:30 | 25 | [304] Jessica Pieri v Manon Arcangioli [260] | Retired | |
| ITF - Trnava W25 | 02/05 10:10 | 25 | Jessica Pieri v Viktoria Morvayova | 2-6,5-7 | |
| ITF - Vero Beach W25 | 01/21 16:00 | 54 | [330] Jessica Pieri v Yuxuan Zhang [444] | 4-6,0-6 | |
| ITF - Vero Beach W25 | 01/20 16:00 | 54 | Jessica Pieri v Meiling Wang | 6-2,6-0 | |
| ITF - Malibu W25 | 01/18 19:00 | 28 | [328] Jessica Pieri v Nadia Podoroska [258] | 1-6,1-6 | |
| ITF - Malibu W25 | 01/17 19:00 | 27 | [328] Jessica Pieri v Catherine Harrison [289] | 6-2,6-7,7-5 | |
| ITF - Malibu W25 | 01/16 20:00 | 26 | [328] Jessica Pieri v Katie Volynets [394] | 6-3,2-6,6-4 | |
| ITF - Malibu W25 | 01/15 19:00 | 25 | [328] Jessica Pieri v Kayla Day [423] | 6-1,3-6,7-6 | |
| ITF - Solarino W25 | 11/26 09:00 | 25 | Jessica Pieri v Federica Rossi | Cancelled | |
| ITF - Mińsk W25 | 11/15 08:40 | 27 | [206] Marina Melnikova v Jessica Pieri [339] | 6-0,6-3 | |
| ITF - Mińsk W25 | 11/14 07:00 | 26 | [339] Jessica Pieri v Nicoleta-Catalina Dascalu [290] | 4-6,6-2,6-2 | |
| ITF - Mińsk W25 | 11/13 07:00 | 25 | Jessica Pieri v Anastasiya Komar | 7-6,6-4 | |
| ITF - Seville W25 | 10/16 09:00 | 25 | [352] Amanda Carreras v Jessica Pieri [343] | 4-6,6-1,7-5 | |
| ITF - Santa Margherita W25 | 10/09 13:30 | 26 | [347] Jessica Pieri v Amina Anshba [338] | 1-6,7-5,6-7 | |
| ITF - Santa Margherita W25 | 10/08 11:50 | 25 | Jessica Pieri v Anita Husaric | 6-3,6-1 | |
| ITF - Santa Margherita W25 | 10/02 13:50 | 25 | [342] Jessica Pieri v Maiar Sherif [244] | 2-6,2-6 | |
| ITF - Santa Margherita W25 | 09/20 12:00 | 27 | [415] Amanda Carreras v Jessica Pieri [350] | 6-4,6-1 |