| ITF W25 Kursumlijska Banja | 06/07 14:45 | 25 | [189] Valentini Grammatikopoulou v Sandra Samir [337] | 6-3,6-1 | |
| ITF W40 Otocec | 06/04 08:00 | 29 | [222] Rebecca Sramkova v Valentini Grammatikopoulou [189] | 4-6,4-6 | |
| ITF W40 Otocec | 06/03 10:20 | 28 | [472] Ilinca D Amariei v Valentini Grammatikopoulou [189] | 4-6,6-4,6-7 | |
| ITF W40 Otocec | 06/02 10:10 | 27 | [343] Seone Mendez v Valentini Grammatikopoulou [189] | 3-6,6-1,4-6 | |
| ITF W40 Otocec | 06/01 09:55 | 26 | Dimitra Pavlou v Valentini Grammatikopoulou | 6-4,1-6,2-6 | |
| ITF W40 Otocec | 05/31 13:25 | 25 | Gina Feistel v Valentini Grammatikopoulou | 6-3,1-6,4-6 | |
| French Open - nők | 05/24 09:35 | 15 | [112] Nao Hibino v Valentini Grammatikopoulou [186] | 6-1,6-1 | |
| French Open - nők | 05/22 09:45 | 14 | [186] Valentini Grammatikopoulou v Sinja Kraus [151] | 6-4,6-1 | |
| ITF W60 Zagreb | 05/10 08:00 | 26 | [109] Diane Parry v Valentini Grammatikopoulou [221] | 6-4,6-7,6-1 | |
| ITF W60 Zagreb | 05/09 08:00 | 25 | [221] Valentini Grammatikopoulou v Maja Chwalinska [345] | 7-5,5-7,6-4 | |
| ITF W25 Santa Margherita | 05/07 08:00 | 29 | [347] Kathinka Von Deichmann v Valentini Grammatikopoulou [207] | 4-6,1-6 | |
| ITF W25 Santa Margherita | 05/06 08:00 | 28 | Federica Bilardo v Valentini Grammatikopoulou | 3-6,2-6 | |
| ITF W25 Santa Margherita | 05/05 08:00 | 27 | Anastasia Abbagnato v Valentini Grammatikopoulou | 3-6,4-6 | |
| ITF W25 Santa Margherita | 05/04 09:40 | 26 | Claudia Hoste Ferrer v Valentini Grammatikopoulou | 1-6,5-7 | |
| ITF W25 Santa Margherita | 05/03 15:05 | 25 | Margherita Marcon v Valentini Grammatikopoulou | 2-6,0-6 | |
| ITF W60 Bellinzona | 04/19 13:40 | 25 | [205] Valentini Grammatikopoulou v Zeynep Sonmez [242] | 2-6,1-6 | |
| Billie Jean King Cup | 04/15 09:55 | 1 | [374] Elena Malygina v Valentini Grammatikopoulou [202] | 2-6,4-6 | |
| Billie Jean King Cup | 04/14 10:00 | 1 | [202] Valentini Grammatikopoulou v Matilde Jorge [143] | 6-3,6-2 | |
| Billie Jean King Cup | 04/13 10:00 | - | [202] Valentini Grammatikopoulou v Dea Herdzelas [357] | Retired | |
| Billie Jean King Cup | 04/12 10:00 | 1 | Valentini Grammatikopoulou v Elaine Genovese | 6-1,6-2 | |
| Billie Jean King Cup | 04/11 09:50 | 1 | Valentini Grammatikopoulou v Mika Buchnik | 6-2,6-0 | |
| ITF W25 Santa Margherita | 04/07 09:25 | 27 | [248] Weronika Falkowska v Valentini Grammatikopoulou [193] | 4-6,6-4,6-2 | |
| ITF W25 Santa Margherita | 04/06 08:25 | 26 | Georgia Pedone v Valentini Grammatikopoulou | 6-7,4-6 | |
| ITF W25 Santa Margherita | 04/05 08:30 | 25 | Lois Boisson v Valentini Grammatikopoulou | 6-2,4-6,1-6 | |
| ITF W40 Murska Sobota | 03/28 08:00 | 25 | [244] Magali Kempen v Valentini Grammatikopoulou [195] | 6-2,6-4 | |
| ITF W60 Pretoria | 03/15 09:50 | 25 | [198] Valentini Grammatikopoulou v Alice Robbe [274] | 2-6,6-2,1-6 | |
| ITF W40 Bengaluru | 03/08 07:30 | 25 | [419] Rutuja Bhosale v Valentini Grammatikopoulou [198] | 4-6,6-4,6-0 | |
| ITF W25 Bengaluru | 03/04 04:30 | 28 | [197] Valentini Grammatikopoulou v Misaki Doi [306] | 6-1,3-6,6-7 | |
| ITF W25 Bengaluru | 03/03 07:20 | 27 | [197] Valentini Grammatikopoulou v Dea Herdzelas [365] | 6-2,7-5 | |
| ITF W25 Bengaluru | 03/02 04:30 | 26 | [197] Valentini Grammatikopoulou v Rutuja Bhosale [418] | 6-2,5-7,7-5 |