| ITF W25 Montemor-O-Novo | 06/09 16:30 | 25 | [287] Valentini Grammatikopoulou v Hiroko Kuwata [423] | 6-3,6-4 | |
| ITF W25 Kazan | 06/06 07:55 | 29 | [424] Anna Kubareva v Valentini Grammatikopoulou [287] | 6-1,6-3 | |
| ITF W25 Kazan | 06/05 07:00 | 28 | [287] Valentini Grammatikopoulou v Vlada Koval [404] | 6-2,3-6,6-2 | |
| ITF W25 Kazan | 06/04 06:55 | 27 | [452] Alina Charaeva v Valentini Grammatikopoulou [287] | 6-1,0-6,0-6 | |
| ITF W25 Kazan | 06/03 07:00 | 26 | Jasmin Jebawy v Valentini Grammatikopoulou | 3-6,2-6 | |
| ITF W25 Kazan | 06/02 07:00 | 25 | Anastasia Tikhonova v Valentini Grammatikopoulou | 2-6,1-6 | |
| ITF W25 Liepaja - nők | 05/28 07:55 | 26 | [464] Malene Helgo v Valentini Grammatikopoulou [287] | 7-5,6-4 | |
| ITF W25 Liepaja - nők | 05/26 10:30 | 25 | Vanda Lukacs v Valentini Grammatikopoulou | Retired | |
| ITF W25 Oeiras | 04/30 09:50 | 27 | [464] Maria Gutierrez Carrasco v Valentini Grammatikopoulou [279] | 6-7,7-6,6-3 | |
| ITF W25 Oeiras | 04/29 09:55 | 25 | [279] Valentini Grammatikopoulou v Conny Perrin [272] | 6-4,6-2 | |
| ITF W25 Oeiras | 04/28 12:40 | 28 | Valentini Grammatikopoulou v Yvonne Cavalle-Reimers | 6-4,6-0 | |
| ITF 60 Oeras - női | 04/14 14:05 | 25 | [192] Francesca Jones v Valentini Grammatikopoulou [278] | 6-3,4-6,6-3 | |
| ITF 60 Oeras - női | 04/13 15:30 | 24 | [314] Federica Di Sarra v Valentini Grammatikopoulou [278] | 1-6,2-6 | |
| ITF W25 Cordoba | 04/07 18:35 | 25 | Yvonne Cavalle-Reimers v Valentini Grammatikopoulou | 6-2,6-7,6-2 | |
| ITF W25 Villa Maria | 04/01 14:40 | 26 | [446] Maria Lourdes Carle v Valentini Grammatikopoulou [274] | 7-5,6-4 | |
| ITF W25 Villa Maria | 03/30 15:30 | 25 | [324] Laura Pigossi v Valentini Grammatikopoulou [274] | 3-6,5-7 | |
| ITF W25 Buenos Aires | 03/24 15:05 | 25 | Panna Udvardy v Valentini Grammatikopoulou | 6-1,6-4 | |
| ITF W25 Kazan | 03/12 06:55 | 27 | Anastasia Tikhonova v Valentini Grammatikopoulou | 6-2,4-6,6-4 | |
| ITF W25 Kazan | 03/11 09:30 | 26 | [274] Valentini Grammatikopoulou v Sofya Lansere [270] | 7-5,6-1 | |
| ITF W25 Kazan | 03/10 11:45 | 25 | Valentini Grammatikopoulou v Daria Mishina | 7-5,7-5 | |
| ITF W25 Moszkva | 02/23 12:20 | 25 | [273] Valentini Grammatikopoulou v Anastasia Zakharova [262] | 4-6,6-7 | |
| ITF W25 Altenkirchen | 02/15 14:30 | 45 | [272] Valentini Grammatikopoulou v Ylena In-Albon [426] | 3-6,2-6 | |
| ITF W25 Altenkirchen | 02/14 16:00 | 45 | Valentini Grammatikopoulou v Emily Webley-Smith | 6-4,7-6 | |
| ITF W60 Andrezieux-Boutheon | 01/25 12:25 | 54 | [477] Ana Konjuh v Valentini Grammatikopoulou [267] | 7-6,6-1 | |
| ITF W25 Hamburg | 01/13 13:35 | 25 | [269] Valentini Grammatikopoulou v Nicoleta-Catalina Dascalu [286] | 6-3,2-6,2-6 | |
| WTA Abu Dhabi | 01/07 10:40 | 24 | [269] Valentini Grammatikopoulou v Alize Cornet [53] | 2-6,2-6 | |
| WTA Abu Dhabi | 01/06 07:50 | 19 | [269] Valentini Grammatikopoulou v Kateryna Bondarenko [285] | 1-6,3-6 | |
| WTA Abu Dhabi | 01/05 08:45 | 64 | [269] Valentini Grammatikopoulou v Luisa Stefani [33] | 6-4,1-6,6-1 | |
| ITF W100 Dubai | 12/06 07:40 | 54 | [268] Valentini Grammatikopoulou v Elena Gabriela Ruse [177] | 2-6,5-7 | |
| ITF W25 Istanbul | 10/27 07:00 | 25 | [259] Tena Lukas v Valentini Grammatikopoulou [266] | 6-2,4-6,6-2 |