| ITF W60 Liepaja | 07/15 11:30 | 27 | [252] Anna Siskova v Valentini Grammatikopoulou [193] | 7-6,7-5 | |
| ITF W60 Liepaja | 07/14 09:40 | 26 | Beatrise Zeltina v Valentini Grammatikopoulou | 1-6,1-6 | |
| ITF W60 Liepaja | 07/13 09:45 | 25 | [395] Marine Partaud v Valentini Grammatikopoulou [193] | 6-4,3-6,6-7 | |
| WTA Bastad | 07/05 08:30 | 25 | [187] Valentini Grammatikopoulou v Panna Udvardy [100] | 2-6,5-7 | |
| Wimbledon - nők | 06/21 11:55 | 14 | [191] Valentini Grammatikopoulou v Priscilla Hon [192] | 6-2,4-6,5-7 | |
| ITF W100 Ilkley | 06/14 10:00 | 25 | [189] Valentini Grammatikopoulou v Daria Snigur [132] | 3-6,3-6 | |
| WTA Hertogenbosch | 06/06 08:00 | 19 | [229] Catherine McNally v Valentini Grammatikopoulou [170] | 6-1,6-2 | |
| WTA Hertogenbosch | 06/04 15:20 | 14 | [262] Indy De Vroome v Valentini Grammatikopoulou [187] | 2-6,4-6 | |
| French Open - nők | 05/23 09:00 | 23 | [187] Valentini Grammatikopoulou v Daria Saville [127] | 1-6,2-6 | |
| French Open - nők | 05/20 12:15 | 19 | [188] Valentini Grammatikopoulou v Christina McHale [256] | 6-3,6-3 | |
| French Open - nők | 05/18 15:25 | 15 | [229] Isabella Shinikova v Valentini Grammatikopoulou [188] | 6-2,0-6,3-6 | |
| French Open - nők | 05/17 09:55 | 14 | [188] Valentini Grammatikopoulou v Valeria Savinykh [271] | 6-4,6-1 | |
| ITF W60 Saint-Gaudens | 05/11 07:40 | 25 | [305] Sada Nahimana v Valentini Grammatikopoulou [188] | 6-4,6-4 | |
| ITF W60 Prague | 05/02 12:10 | 25 | [183] Valentini Grammatikopoulou v Susan Bandecchi [194] | 4-6,2-6 | |
| ITF W25 Cairo | 04/29 09:00 | 27 | [385] Weronika Falkowska v Valentini Grammatikopoulou [183] | 6-3,1-6,6-0 | |
| ITF W25 Cairo | 04/28 10:45 | 26 | Antonia Schmidt v Valentini Grammatikopoulou | 3-6,0-6 | |
| ITF W25 Cairo | 04/27 12:55 | 25 | [452] Melanie Klaffner v Valentini Grammatikopoulou [183] | 2-6,6-4,4-6 | |
| ITF W60 Charlottesville | 04/20 13:55 | 25 | [183] Valentini Grammatikopoulou v Xiyu Wang [127] | 3-6,0-6 | |
| ITF W100 Palm Harbor | 04/14 15:35 | 26 | [196] Grace Min v Valentini Grammatikopoulou [193] | 7-5,6-2 | |
| ITF W100 Palm Harbor | 04/13 16:40 | 25 | [193] Valentini Grammatikopoulou v Whitney Osuigwe [275] | 4-6,6-2,6-4 | |
| WTA Bogota | 04/03 17:30 | 19 | [186] Valentini Grammatikopoulou v Ipek Oz [268] | 5-7,4-6 | |
| WTA Bogota | 04/02 15:00 | 45 | [186] Valentini Grammatikopoulou v Maria Paulina Perez Garcia [398] | 6-3,6-3 | |
| ITF W60 Irapuato | 03/10 20:00 | 26 | [187] Valentini Grammatikopoulou v Seone Mendez [205] | 2-6,1-6 | |
| ITF W60 Irapuato | 03/08 20:00 | 25 | [187] Valentini Grammatikopoulou v Peangtarn Plipuech [420] | 6-2,2-6,6-1 | |
| WTA Lyon | 02/26 17:35 | 14 | [188] Valentini Grammatikopoulou v Laura Siegemund [158] | 1-6,4-6 | |
| ITF W25 Porto | 02/17 12:10 | 26 | [189] Valentini Grammatikopoulou v Adrienn Nagy [315] | 6-4,4-6,4-6 | |
| ITF W25 Porto | 02/15 16:05 | 25 | [189] Valentini Grammatikopoulou v Angela Fita Boluda [407] | 6-2,6-3 | |
| ITF W25 Porto | 02/10 10:00 | 26 | Valentini Grammatikopoulou v Julia Terziyska | 5-7,3-6 | |
| ITF W25 Porto | 02/08 11:40 | 25 | [191] Valentini Grammatikopoulou v Matilde Jorge [435] | 5-7,7-5,6-0 | |
| ITF W25 Cairo | 01/26 13:15 | 25 | Valentini Grammatikopoulou v Anastasia Nefedova | 7-5,6-7,4-6 |