| ITF W25 Getxo | 07/06 11:55 | 25 | [474] Jessica Pieri v Ana Sofia Sanchez [334] | 6-4,6-3 | |
| ITF W25 Den Haag | 06/29 17:35 | 25 | Martha Matoula v Jessica Pieri | 6-4,6-3 | |
| Wimbledon Women | 06/22 15:25 | 15 | [478] Jessica Pieri v Nastasja Schunk [156] | 5-7,3-6 | |
| Wimbledon Women | 06/21 16:15 | 14 | [478] Jessica Pieri v Giulia Gatto Monticone [280] | 6-4,6-2 | |
| WTA Courmayeur | 10/26 12:45 | 25 | [284] Jessica Pieri v Shuai Zhang [58] | 1-6,3-6 | |
| ITF W25 Seville | 10/20 08:30 | 26 | Leyre R Gormaz v Jessica Pieri | 7-6,6-1 | |
| ITF W25 Seville | 10/19 10:35 | 25 | [401] Miriam B Bulgaru v Jessica Pieri [280] | 0-6,3-6 | |
| ITF W25 Lagos | 10/14 10:00 | 26 | [279] Jessica Pieri v Jessika Ponchet [213] | 1-6,5-7 | |
| ITF W25 Lagos | 10/13 09:30 | 25 | Jessica Pieri v Tina Cvetkovic | 6-3,6-3 | |
| ITF W25 Lagos | 10/13 09:30 | 25 | [279] Jessica Pieri v Francisca Jorge [378] | Cancelled | |
| ITF W25 Loule | 10/07 11:15 | 26 | [279] Jessica Pieri v Natalija Stevanovic [259] | Retired | |
| ITF W25 Loule | 10/06 15:20 | 25 | [279] Jessica Pieri v Francisca Jorge [378] | 7-5,6-4 | |
| ITF W80 Wiesbaden | 09/22 08:30 | 25 | Jessica Pieri v Anna Klasen | Cancelled | |
| ITF W25 Jablonec nad Nisou | 09/17 11:05 | 27 | Jessica Pieri v Aneta Kladivova | 6-4,4-6,5-7 | |
| ITF W25 Jablonec nad Nisou | 09/16 10:00 | 26 | [271] Jessica Pieri v Alexandra Bozovic [442] | 7-6,7-6 | |
| ITF W25 Jablonec nad Nisou | 09/14 11:25 | 25 | [271] Jessica Pieri v Lara Salden [346] | 6-0,6-3 | |
| ITF W60 Montreux | 09/09 15:20 | 26 | [170] Francesca Jones v Jessica Pieri [260] | 6-2,4-6,6-1 | |
| ITF W60 Montreux | 09/07 12:35 | 25 | [410] Stefania Rubini v Jessica Pieri [260] | 3-6,5-7 | |
| ITF W25 Vienna | 09/02 12:10 | 26 | Erika Andreeva v Jessica Pieri | 6-3,6-3 | |
| ITF W25 Vienna | 08/31 11:30 | 25 | [451] Ekaterina Kazionova v Jessica Pieri [259] | 6-3,4-6,3-6 | |
| US Open Women | 08/25 22:00 | 14 | [102] Oceane Dodin v Jessica Pieri [258] | 6-1,6-3 | |
| WTA Cluj-Napoca | 08/01 11:10 | 14 | Vanessa I G Popa Teiusanu v Jessica Pieri | 7-6,7-5 | |
| ITF W60 Grodzisk Mazowiecki | 07/30 08:00 | 25 | [249] Chloe Paquet v Jessica Pieri [250] | Cancelled | |
| ITF W60 Olomouc | 07/22 08:00 | 26 | [245] Jessica Pieri v Nika Radisic [287] | 6-0,1-6,2-6 | |
| ITF W60 Olomouc | 07/21 13:20 | 25 | [245] Jessica Pieri v Seone Mendez [272] | Retired | |
| ITF W100 Contrexeville | 07/07 17:00 | 25 | Jessica Pieri v Lois Boisson | 4-6,1-6 | |
| ITF W25 The Hague | 07/01 07:30 | 25 | Quirine Lemoine v Jessica Pieri | Walkover | |
| Wimbledon Women | 06/23 10:00 | 14 | [243] Jessica Pieri v Barbara Haas [157] | 4-6,6-2,0-6 | |
| ITF W25 Denain | 06/16 09:30 | 25 | [250] Jessica Pieri v Ylena In-Albon [450] | 6-2,4-6,4-6 | |
| ITF W25 Madrid | 06/12 10:10 | 28 | [249] Jessica Pieri v Robin Anderson [215] | 3-6,6-2,1-6 |