| ITF Women Shenzhen | 11/09 04:05 | 27 | [46] Saisai Zheng v Valentini Grammatikopoulou [165] | 6-2,6-1 | |
| ITF Women Shenzhen | 11/08 04:15 | 26 | [191] Elena Rybakina v Valentini Grammatikopoulou [165] | 4-6,6-3,3-6 | |
| ITF Women Shenzhen | 11/06 04:15 | 25 | [165] Valentini Grammatikopoulou v Nao Hibino [119] | 6-3,6-4 | |
| WTA Mumbai | 11/02 14:35 | 27 | [165] Irina Khromacheva v Valentini Grammatikopoulou [171] | 7-5,4-6,6-1 | |
| WTA Mumbai | 10/31 10:30 | 26 | [171] Valentini Grammatikopoulou v Deniz Khazaniuk [252] | 6-3,4-6,6-4 | |
| WTA Mumbai | 10/30 09:05 | 25 | Kwan Yau Ng v Valentini Grammatikopoulou | 0-6,2-6 | |
| WTA Moszkva | 10/17 10:45 | 26 | [170] Valentini Grammatikopoulou v Anastasia Pavlyuchenkova [40] | 5-7,0-6 | |
| WTA Moszkva | 10/15 08:00 | 54 | [101] Ons Jabeur v Valentini Grammatikopoulou [170] | 7-5,6-1 | |
| WTA Moszkva | 10/14 09:00 | 46 | [171] Valentini Grammatikopoulou v Georgina Garcia-Perez [126] | 6-1,6-2 | |
| WTA Moszkva | 10/13 07:00 | 45 | [171] Valentini Grammatikopoulou v Alexandra Panova [477] | 6-7,6-4,6-4 | |
| WTA Linz | 10/09 14:00 | 25 | [97] Kristyna Pliskova v Valentini Gramma'poulou [171] | 6-4,6-2 | |
| WTA Linz | 10/08 09:00 | 46 | [171] Valentini Gramma'poulou v Vitalia Diatchenko [117] | 6-2,7-5 | |
| WTA Linz | 10/07 12:10 | 45 | [88] Carina Witthoeft v Valentini Gramma'poulou [172] | 7-6,2-6,3-6 | |
| ITF Women Valencia | 09/26 09:00 | 25 | [291] Andrea Gamiz v Valentini Grammatikopoulou [171] | 3-6,6-4,6-2 | |
| ITF Women Zagreb | 09/06 10:55 | 26 | Kaja Juvan v Valentini Grammatikopoulou | 6-3,6-2 | |
| ITF Women Zagreb | 09/05 10:55 | 25 | Lea Boskovic v Valentini Grammatikopoulou | 3-6,6-7 | |
| ITF Women Bagnatica | 08/31 12:30 | 27 | [169] Valentini Grammatikopoulou v Jasmine Paolini [229] | 2-6,3-6 | |
| ITF Women Bagnatica | 08/29 12:00 | 26 | [169] Valentini Grammatikopoulou v Marie Benoit [295] | 7-6,6-4 | |
| ITF Women Bagnatica | 08/28 14:20 | 25 | Valentini Grammatikopoulou v Camilla Scala | 4-6,6-1,6-1 | |
| US Open - nők | 08/21 15:00 | 44 | [169] Valentini Grammatikopoulou v Silvia Soler-Espinosa [190] | 4-6,6-7 | |
| ITF Women Chiswick | 08/11 10:00 | 29 | [106] Vitalia Diatchenko v Valentini Grammatikopoulou [181] | 6-1,7-5 | |
| ITF Women Chiswick | 08/10 09:30 | 28 | [181] Valentini Grammatikopoulou v Samantha Murray [300] | 6-2,2-6,6-2 | |
| ITF Women Chiswick | 08/09 11:30 | 27 | Lesley Kerkhove v Valentini Grammatikopoulou | 6-3,1-6,3-6 | |
| ITF Women Chiswick | 08/08 11:55 | 26 | [499] Linnea Malmqvist v Valentini Grammatikopoulou [181] | Retired | |
| ITF Women Chiswick | 08/07 09:30 | 25 | [415] Angelica Moratelli v Valentini Grammatikopoulou [181] | 6-7,6-1,4-6 | |
| ITF Women Woking | 08/03 11:30 | 28 | [242] Ivana Jorovic v Valentini Grammatikopoulou [180] | 5-7,6-4,6-0 | |
| ITF Women Woking | 08/02 11:35 | 27 | [247] Giulia G-Monticone v Valentini Grammatikopoulou [180] | 6-4,1-6,0-6 | |
| ITF Women Woking | 08/01 11:10 | 26 | [309] Dalma Galfi v Valentini Grammatikopoulou [180] | 4-6,3-6 | |
| ITF Women Woking | 07/31 15:20 | 25 | Vlada Ekshibarova v Valentini Grammatikopoulou | 5-7,7-5,4-6 | |
| WTA Moszkva | 07/24 11:45 | 25 | [181] Valentini Grammatikopoulou v Varvara Flink [318] | 2-6,6-3,3-6 |