| ITF W25 Bengaluru | 03/01 06:10 | 25 | [197] Valentini Grammatikopoulou v Elena-Teodora Cadar [413] | 6-2,5-7,6-4 | |
| ITF W40 Porto | 02/09 12:55 | 26 | [200] Valentini Grammatikopoulou v Harmony Tan [162] | 2-6,4-6 | |
| ITF W40 Porto | 02/07 12:05 | 25 | Sara Lanca v Valentini Grammatikopoulou | 0-6,3-6 | |
| ITF W40 Porto | 01/31 13:45 | 25 | [204] Valentini Grammatikopoulou v Lucia Cortez Llorca [473] | 4-6,2-6 | |
| ITF W25 Monastir | 01/27 08:30 | 27 | [200] Valentini Grammatikopoulou v Lola Radivojevic [337] | 3-6,2-6 | |
| ITF W25 Monastir | 01/26 08:30 | 26 | Valentini Grammatikopoulou v Chia Yi Tsao | 6-2,6-2 | |
| ITF W25 Monastir | 01/24 10:30 | 25 | Valentini Grammatikopoulou v Tereza Mrdeza | 6-1,6-3 | |
| Ausztrál Open - nők | 01/10 01:00 | 14 | [201] Valentini Grammatikopoulou v Marina B Ribera [125] | 2-6,1-6 | |
| United Cup - nők | 01/07 09:10 | 28 | [199] Valentini Grammatikopoulou v Lucia Bronzetti [54] | 2-6,3-6 | |
| ITF W60 Meitar | 11/16 09:35 | 26 | [405] Mirra Andreeva v Valentini Grammatikopoulou [200] | 6-2,6-2 | |
| ITF W60 Meitar | 11/15 11:30 | 25 | Mika Buchnik v Valentini Grammatikopoulou | 4-6,4-6 | |
| ITF W60 Nantes | 10/31 15:00 | 25 | [135] Clara Tauson v Valentini Grammatikopoulou [200] | 6-1,7-5 | |
| ITF W25 Sozopol | 10/18 07:00 | 25 | [201] Valentini Grammatikopoulou v Andreea Prisacariu [419] | 6-3,1-6,6-7 | |
| ITF W60 Trnava | 10/13 08:35 | 26 | [207] Valentini Grammatikopoulou v Vitalia Diatchenko [112] | 4-6,4-6 | |
| ITF W60 Trnava | 10/11 13:00 | 25 | [207] Valentini Grammatikopoulou v Mona Barthel [260] | 6-4,7-6 | |
| ITF W60 Trnava | 10/06 09:25 | 26 | [197] Valentini Grammatikopoulou v Maia Lumsden [272] | 6-4,4-6,3-6 | |
| ITF W60 Trnava | 10/05 08:00 | 25 | [197] Valentini Grammatikopoulou v Kathleen Kanev [465] | 6-3,6-0 | |
| WTA Tallinn | 09/24 15:45 | 14 | [133] Mirjam Bjorklund v Valentini Grammatikopoulou [200] | 6-2,6-2 | |
| WTA Seoul | 09/18 03:00 | 19 | [194] Valentini Grammatikopoulou v Ankita Raina [325] | 6-7,7-6,0-6 | |
| WTA Seoul | 09/17 02:15 | 14 | [194] Valentini Grammatikopoulou v Nadiia Kichenok [105] | 7-5,6-7,6-0 | |
| WTA Vancouver | 08/21 19:00 | 29 | [239] Valentini Grammatikopoulou v Lucia Bronzetti [66] | 6-2,6-4 | |
| WTA Vancouver | 08/20 19:25 | 28 | [168] Emma Navarro v Valentini Grammatikopoulou [239] | 4-6,6-3,1-6 | |
| WTA Vancouver | 08/19 18:00 | 27 | [239] Valentini Grammatikopoulou v Chloe Paquet [111] | 6-3,6-4 | |
| WTA Vancouver | 08/17 17:00 | 26 | Cadence Brace v Valentini Grammatikopoulou | 5-7,2-6 | |
| WTA Vancouver | 08/15 20:55 | 25 | [192] Astra Sharma v Valentini Grammatikopoulou [239] | 2-6,2-6 | |
| WTA Vancouver | 08/14 17:00 | 19 | [187] Asia Muhammad v Valentini Grammatikopoulou [236] | 6-2,5-7,2-6 | |
| WTA Vancouver | 08/13 17:00 | 14 | [406] Nagi Hanatani v Valentini Grammatikopoulou [236] | 3-6,6-1,2-6 | |
| WTA Toronto | 08/06 15:00 | 14 | [46] Marie Bouzkova v Valentini Grammatikopoulou [235] | 6-2,6-0 | |
| WTA Washington | 07/30 19:50 | 14 | [109] Rebecca Marino v Valentini Grammatikopoulou [188] | 6-0,4-6,6-2 | |
| ITF W25 Saskatoon | 07/19 18:15 | 25 | Valentini Grammatikopoulou v Victoria Mboko | 7-6,1-6,3-6 |