Stadium: Court 1 Round: 14 Ground: Clay
| WTA Budapest | 2023/07/18 09:00 | Valentini Grammatikopoulou v Tamara Korpatsch | 4-6,4-6 |
| WTA Budapest | 2023/07/16 11:00 | Valentini Grammatikopoulou v Astra Sharma | 3-6,1-6 |
| WTA Budapest | 2023/07/15 11:30 | Valentini Grammatikopoulou v Adrienn Nagy | 6-2,3-6,6-4 |
| WTA Contrexeville | 2023/07/10 13:00 | Aleksandra Krunic v Valentini Grammatikopoulou | 6-2,3-6,6-4 |
| ITF W60 Liepaja | 2023/07/05 10:30 | Dejana Radanovic v Valentini Grammatikopoulou | 7-6,6-2 |
| Wimbledon Women | 2023/06/27 15:45 | Valentini Grammatikopoulou v Natalija Stevanovic | 2-6,1-6 |
| ITF W100 Ilkley | 2023/06/21 13:30 | Valentini Grammatikopoulou v Nao Hibino | 5-7,1-6 |
| ITF W25 Kursumlijska Banja | 2023/06/09 10:05 | Valentini Grammatikopoulou v Dimitra Pavlou | 5-7,3-6 |
| ITF W25 Don Benito | 2023/07/16 08:30 | Valentina Ryser v Tamira Paszek | 6-7,7-6,6-7 |
| ITF W25 Don Benito | 2023/07/15 10:20 | Zeynep Sonmez v Valentina Ryser | 3-6,5-7 |
| ITF W25 Don Benito | 2023/07/14 07:55 | Pemra Ozgen v Valentina Ryser | 6-4,0-6,6-7 |
| ITF W25 Don Benito | 2023/07/13 08:10 | Maria B Bandera v Valentina Ryser | 2-6,1-6 |
| ITF W25 Don Benito | 2023/07/11 08:50 | Carolina Gomez v Valentina Ryser | 4-6,4-6 |
| ITF W25 Cantanhede | 2023/07/07 13:15 | Valentina Ryser v Arina Rodionova | 6-7,1-6 |
| ITF W25 Cantanhede | 2023/07/06 10:00 | Katy Dunne v Valentina Ryser | 4-6,2-6 |
| ITF W25 Cantanhede | 2023/07/04 10:00 | Valentina Ryser v Diana Marcinkevica | 6-4,6-2 |