| ITF - W25 Hamburgo | 01/14 10:00 | 26 | Jessica Pieri v Noma Noha Akugue | 1-6,3-6 | |
| ITF - W25 Hamburgo | 01/12 16:15 | 25 | Nastasja M Schunk v Jessica Pieri | 7-5,4-6,3-6 | |
| WTA - Abu Dabi | 01/06 06:00 | 19 | [275] Anna Bondar v Jessica Pieri [294] | 4-6,6-4,7-5 | |
| WTA - Abu Dabi | 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 - Roma | 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 | |
| Italian Umbrian Open - Feminino | 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 |