| ITF W25 Sharm El Sheikh | 10/28 08:00 | 28 | Valentini Grammatikopoulou v Marina Melnikova | 4-6,7-5,6-1 | |
| ITF W25 Sharm El Sheikh | 10/27 08:00 | 27 | Valentini Grammatikopoulou v Karola Patricia Bejenaru | 6-1,7-5 | |
| ITF W25 Sharm El Sheikh | 10/26 07:00 | 26 | Valentini Grammatikopoulou v Lamis Alhussein Abdel Aziz | 6-3,0-6,7-5 | |
| ITF W25 Sharm El Sheikh | 10/25 06:30 | 25 | Valentini Grammatikopoulou v Alisa Kummel | 4-6,6-2,6-3 | |
| WTA Cluj-Napoca | 10/14 08:00 | 14 | [398] Susan Bandecchi v Valentini Grammatikopoulou [238] | 6-3,4-6,7-5 | |
| ITF W25 Slobozia | 09/23 11:40 | 28 | [241] Valentini Grammatikopoulou v Ekaterina Vl. Makarova [240] | 3-6,0-6 | |
| ITF W25 Slobozia | 09/22 08:25 | 27 | [261] Anca Alexia Todoni v Valentini Grammatikopoulou [241] | Retired | |
| ITF W25 Slobozia | 09/21 08:45 | 26 | Viktoriia Dema v Valentini Grammatikopoulou | 6-4,2-6,3-6 | |
| ITF W25 Slobozia | 09/19 11:10 | 25 | [496] Tiphanie Lemaitre v Valentini Grammatikopoulou [241] | Retired | |
| WTA Bucharest | 09/12 12:20 | 25 | [247] Valentini Grammatikopoulou v Anna Bondar [110] | 3-6,6-2,4-6 | |
| WTA Bari | 09/06 16:10 | 26 | [79] Alize Cornet v Valentini Grammatikopoulou [247] | 4-6,6-4,7-5 | |
| WTA Bari | 09/05 10:00 | 25 | [247] Valentini Grammatikopoulou v Giorgia Pedone [388] | 6-4,6-2 | |
| US Open - nők | 08/23 20:15 | 14 | [247] Valentini Grammatikopoulou v Haruka Kaji [222] | 3-6,3-6 | |
| WTA Barranquilla | 08/16 20:40 | 26 | [58] Tatjana Maria v Valentini Grammatikopoulou [164] | 6-0,6-2 | |
| WTA Barranquilla | 08/14 20:30 | 25 | [360] Katarina Kozarov v Valentini Grammatikopoulou [164] | 3-6,2-6 | |
| ITF W25 Koge | 08/05 09:00 | 28 | [173] Valentini Grammatikopoulou v Hanne Vandewinkel [461] | 3-6,3-6 | |
| ITF W25 Koge | 08/04 09:35 | 27 | [173] Valentini Grammatikopoulou v Dejana Radanovic [464] | 1-6,6-3,6-4 | |
| ITF W25 Koge | 08/03 08:00 | 26 | Valentini Grammatikopoulou v Anouk Koevermans | 1-6,7-6,6-2 | |
| ITF W25 Koge | 08/01 10:05 | 25 | [173] Valentini Grammatikopoulou v Anca Alexia Todoni [441] | 6-2,7-6 | |
| WTA Lausanne | 07/25 10:05 | 25 | [170] Valentini Grammatikopoulou v Dalila Jakupovic [267] | 6-7,2-6 | |
| WTA Lausanne | 07/24 09:00 | 14 | [170] Valentini Grammatikopoulou v Valentina Ryser [386] | 6-1,6-3 | |
| WTA Budapest | 07/18 09:00 | 25 | [170] Valentini Grammatikopoulou v Tamara Korpatsch [99] | 4-6,4-6 | |
| WTA Budapest | 07/16 11:00 | 19 | [164] Valentini Grammatikopoulou v Astra Sharma [255] | 3-6,1-6 | |
| WTA Budapest | 07/15 11:30 | 45 | [164] Valentini Grammatikopoulou v Adrienn Nagy [314] | 6-2,3-6,6-4 | |
| WTA Contrexeville | 07/10 13:00 | 25 | [212] Aleksandra Krunic v Valentini Grammatikopoulou [164] | 6-2,3-6,6-4 | |
| ITF W60 Liepaja | 07/05 10:30 | 25 | Dejana Radanovic v Valentini Grammatikopoulou | 7-6,6-2 | |
| Wimbledon - nők | 06/27 15:45 | 14 | [164] Valentini Grammatikopoulou v Natalija Stevanovic [223] | 2-6,1-6 | |
| ITF W100 Ilkley | 06/21 13:30 | 25 | [164] Valentini Grammatikopoulou v Nao Hibino [125] | 5-7,1-6 | |
| ITF W25 Kursumlijska Banja | 06/09 10:05 | 27 | Valentini Grammatikopoulou v Dimitra Pavlou | 5-7,3-6 | |
| ITF W25 Kursumlijska Banja | 06/08 07:00 | 26 | Valentini Grammatikopoulou v Aysegul Mert | 6-3,6-2 |