| US Open Women | 08/19 15:00 | 44 | [196] Maddison Inglis v Valentini Grammatikopoulou [221] | 6-3,6-4 | |
| ITF M25 Chiswick | 08/10 10:30 | 28 | [207] Valentini Grammatikopoulou v Samantha Murray [337] | 4-6,2-6 | |
| ITF M25 Chiswick | 08/09 10:30 | 27 | Irys Ekani v Valentini Grammatikopoulou | 6-3,4-6,2-6 | |
| ITF M25 Chiswick | 08/08 09:00 | 26 | Yuriko Lily Miyazaki v Valentini Grammatikopoulou | 3-6,6-4,6-7 | |
| ITF M25 Chiswick | 08/06 11:00 | 25 | Ali Collins v Valentini Grammatikopoulou | 1-6,6-2,0-6 | |
| WTA Lausanne | 07/13 09:55 | 45 | Pauline Wuarin v Valentini Grammatikopoulou | 1-6,6-4,6-3 | |
| ITF W60 Versmold | 07/11 11:00 | 26 | [236] Louisa Chirico v Valentini Grammatikopoulou [193] | 6-4,2-6,7-6 | |
| ITF W60 Versmold | 07/10 12:30 | 25 | Anastasiya Shoshyna v Valentini Grammatikopoulou | 2-6,2-6 | |
| ITF W25 Den Haag | 07/02 12:15 | 25 | Valentini Gram'lou v Eva Vedder | 2-6,3-6 | |
| Wimbledon Women | 06/25 16:35 | 44 | [194] Valentini Grammatikopoulou v Kaja Juvan [125] | 4-6,6-3,8-10 | |
| ITF W100 Ilkley | 06/18 12:25 | 45 | [175] Robin Anderson v Valentini Grammatikopoulou [193] | 6-1,6-4 | |
| ITF W100 Ilkley | 06/17 14:10 | 45 | [473] Alicia Barnett v Valentini Grammatikopoulou [193] | 6-7,6-2,7-10 | |
| ITF W60 Rome | 06/13 08:30 | 26 | [161] Conny Perrin v Valentini Grammatikopoulou [185] | 6-2,6-2 | |
| ITF W60 Rome | 06/11 13:50 | 25 | Elisabetta Cocciaretto v Valentini Grammatikopoulou | 4-6,4-6 | |
| French Open Women | 05/24 11:15 | 46 | [193] Valentini Grammatikopoulou v Varvara Lepchenko [130] | 2-6,2-6 | |
| French Open Women | 05/23 09:45 | 45 | [105] Heather Watson v Valentini Grammatikopoulou [193] | 5-7,7-6,6-7 | |
| French Open Women | 05/22 08:00 | 44 | [193] Valentini Grammatikopoulou v Kimberly Birrell [158] | 6-2,3-6,6-4 | |
| ITF W60 La Bisbal | 05/15 14:40 | 25 | [120] Marie Bouzkova v Valentini Grammatikopoulou [196] | 6-3,6-2 | |
| ITF W25 Obidos | 05/11 13:30 | 28 | [198] Valentini Grammatikopoulou v Pemra Ozgen [252] | 3-6,4-6 | |
| ITF W25 Obidos | 05/11 09:00 | 27 | [198] Valentini Grammatikopoulou v Monika Kilnarova [324] | 6-0,4-6,6-4 | |
| ITF W25 Obidos | 05/10 13:00 | 26 | Valentini Grammatikopoulou v Lucie Wargnier | 6-4,3-6,6-3 | |
| ITF W25 Obidos | 05/08 13:00 | 25 | Valentini Grammatikopoulou v Anastasia Kulikova | 7-6,6-1 | |
| ITF W60 Wiesbaden | 05/02 12:00 | 26 | [176] Katarina Zavatska v Valentini Grammatikopoulou [198] | 6-4,4-6,6-2 | |
| ITF W60 Wiesbaden | 05/01 09:00 | 25 | [198] Valentini Grammatikopoulou v Julie Gervais [390] | 6-3,1-6,6-4 | |
| WTA Stuttgart | 04/20 09:30 | 45 | [195] Anna Zaja v Valentini Grammatikopoulou [199] | 7-6,7-6 | |
| ITF W60 Istanbul | 04/13 07:30 | 27 | [250] Jana Cepelova v Valentini Grammatikopoulou [178] | 7-5,6-4 | |
| ITF W60 Istanbul | 04/12 07:30 | 26 | [336] Berfu Cengiz v Valentini Grammatikopoulou [178] | 4-6,1-6 | |
| ITF W60 Istanbul | 04/09 11:40 | 25 | Polina Monova v Valentini Grammatikopoulou | Retired | |
| ITF W25 Kofu | 03/20 07:30 | 25 | [453] Sandra Samir v Valentini Grammatikopoulou [174] | 1-6,7-5,7-6 | |
| ITF W25 Nishi-Tama | 03/14 03:50 | 26 | [171] Valentini Gram'lou v Jodie Anna Burrage [345] | 2-6,4-6 |