Stadium: COURT 2 Round: 45 Ground: Hardcourt indoor
| Sofia, Singles W-WITF-BUL-01A | 2016/09/07 07:00 | Valentini Grammatikopoulou v Jessica Pieri | 3-6,5-7 |
| WTA Gstaad Qual | 2018/07/15 09:00 | Veronika Kudermetova v Jessica Pieri | 6-7,6-1,6-2 |
| WTA Gstaad Qual | 2018/07/14 09:50 | Mihail, Diana Maria v Jessica Pieri | 0-6,1-6 |
| ITF Women Versmold | 2018/07/12 12:50 | Jessica Pieri v Olga Danilovic | 1-6,1-6 |
| ITF Women Versmold | 2018/07/10 13:00 | Soylu, Ipek v Jessica Pieri | 2-6,4-6 |
| Rome, Singles W-WITF-ITA-10A | 2018/07/06 11:00 | Soler-Espinosa, Silvia v Jessica Pieri | 7-5,5-7,7-6 |
| Rome, Singles W-WITF-ITA-10A | 2018/07/05 10:00 | Jessica Pieri v Anastasia Grymalska | 6-2,6-3 |
| Rome, Singles W-WITF-ITA-10A | 2018/07/04 08:00 | Jessica Pieri v Skamlova, Chantal | 6-1,6-2 |
| Wimbledon Women Qual | 2018/06/27 10:00 | Caroline Dolehide v Jessica Pieri | 6-2,6-3 |
| ITF Women Getxo | 2018/07/10 09:35 | Valentini Grammatikopoulou v Gonzalez, Montserrat | 6-4,4-6,4-6 |
| ITF Women Denain | 2018/07/07 12:00 | Valentini Grammatikopoulou v Valeriya Strakhova | 6-3,4-6,4-6 |
| ITF Women Denain | 2018/07/06 10:45 | Valentini Grammatikopoulou v Anna Danilina | 6-4,7-6 |
| ITF Women Denain | 2018/07/05 12:45 | Valentini Grammatikopoulou v Alice Rame | 7-6,2-6,6-2 |
| ITF Women Denain | 2018/07/04 08:30 | Valentini Grammatikopoulou v Remondina, Anna | 7-6,6-7,6-2 |
| Wimbledon Women Qual | 2018/06/26 14:40 | Sofya Zhuk v Valentini Grammatikopoulou | 6-3,6-2 |
| WTA - Hertogenbosch | 2018/06/12 09:00 | Valentini Grammatikopoulou v Aleksandra Krunic | 1-6,0-6 |
| s-Hertogenbosch, Netherlands, Qualifying | 2018/06/10 09:00 | Valentini Grammatikopoulou v Piter, Katarzyna | 6-4,6-4 |