| WTA Abu Dhabi | 01/05 08:05 | 64 | [366] Katarzyna Piter v Jessica Pieri [294] | 4-6,0-6 | |
| ITF W25 Porto | 09/27 10:00 | 44 | Jessica Pieri v Ramu Ueda | 5-7,2-6 | |
| WTA Róma | 09/12 09:35 | 14 | [312] Jessica Pieri v Aliona Bolsova [103] | 1-6,1-6 | |
| WTA Prague | 09/03 09:25 | 26 | [312] Jessica Pieri v Ivana Jorovic [230] | Retired | |
| WTA Prague | 09/02 08:00 | 25 | [148] Leonie Kung v Jessica Pieri [312] | 6-1,1-6,4-6 | |
| WTA Prague | 08/31 08:00 | 25 | [312] Jessica Pieri v Daria Lopatetska [381] | 3-6,7-6,6-4 | |
| WTA Prague | 08/29 12:00 | 24 | [335] Irene Burillo Escorihuela v Jessica Pieri [312] | 4-6,5-7 | |
| Italian Umbrian Open - nők | 06/25 08:30 | 1 | Nicole Fossa Huergo v Jessica Pieri | 7-6,6-4 | |
| ITF W25 Altenkirchen | 02/25 15:00 | 25 | Stefania Rubini v Jessica Pieri | Cancelled | |
| ITF W25 Grenoble | 02/13 11:15 | 26 | [304] Jessica Pieri v Amandine Hesse [253] | 6-7,6-7 | |
| ITF W25 Grenoble | 02/11 12:30 | 25 | [304] Jessica Pieri v Manon Arcangioli [260] | Retired | |
| ITF W25 Trnava | 02/05 10:10 | 25 | Jessica Pieri v Viktoria Morvayova | 2-6,5-7 | |
| ITF W25 Vero Beach | 01/21 16:00 | 54 | [330] Jessica Pieri v Yuxuan Zhang [444] | 4-6,0-6 | |
| ITF W25 Vero Beach | 01/20 16:00 | 54 | Jessica Pieri v Meiling Wang | 6-2,6-0 | |
| ITF W25 Malibu | 01/18 19:00 | 28 | [328] Jessica Pieri v Nadia Podoroska [258] | 1-6,1-6 | |
| ITF W25 Malibu | 01/17 19:00 | 27 | [328] Jessica Pieri v Catherine Harrison [289] | 6-2,6-7,7-5 | |
| ITF W25 Malibu | 01/16 20:00 | 26 | [328] Jessica Pieri v Katie Volynets [394] | 6-3,2-6,6-4 | |
| ITF W25 Malibu | 01/15 19:00 | 25 | [328] Jessica Pieri v Kayla Day [423] | 6-1,3-6,7-6 | |
| ITF W25 Solarino | 11/26 09:00 | 25 | Jessica Pieri v Federica Rossi | Cancelled | |
| ITF W25 Minsk | 11/15 08:40 | 27 | [206] Marina Melnikova v Jessica Pieri [339] | 6-0,6-3 | |
| ITF W25 Minsk | 11/14 07:00 | 26 | [339] Jessica Pieri v Nicoleta-Catalina Dascalu [290] | 4-6,6-2,6-2 | |
| ITF W25 Minsk | 11/13 07:00 | 25 | Jessica Pieri v Anastasiya Komar | 7-6,6-4 | |
| ITF W25 Seville | 10/16 09:00 | 25 | [352] Amanda Carreras v Jessica Pieri [343] | 4-6,6-1,7-5 | |
| ITF W25 Santa Margherita | 10/09 13:30 | 26 | [347] Jessica Pieri v Amina Anshba [338] | 1-6,7-5,6-7 | |
| ITF W25 Santa Margherita | 10/08 11:50 | 25 | Jessica Pieri v Anita Husaric | 6-3,6-1 | |
| ITF W25 Santa Margherita | 10/02 13:50 | 25 | [342] Jessica Pieri v Maiar Sherif [244] | 2-6,2-6 | |
| ITF W25 Santa Margherita | 09/20 12:00 | 27 | [415] Amanda Carreras v Jessica Pieri [350] | 6-4,6-1 | |
| ITF W25 Santa Margherita | 09/19 16:45 | 26 | [471] Julyette M J Steur v Jessica Pieri [350] | 0-6,4-6 | |
| ITF W25 Santa Margherita | 09/18 12:00 | 25 | [434] Julia Payola v Jessica Pieri [350] | 4-6,2-6 | |
| ITF W25 Santa Margherita | 09/13 16:00 | 27 | [349] Jessica Pieri v Elisabetta Cocciaretto [417] | 4-6,0-6 |