| ITF W60 Colina | 11/06 18:00 | 25 | [188] Andrea Gamiz v Valentini Gram'lou [265] | 5-7,6-2,5-7 | |
| ITF W60 Asuncion | 10/30 19:00 | 25 | [248] Valentini Grammatikopoulou v Teliana Pereira [417] | 3-6,2-6 | |
| ITF W80 Macon | 10/23 18:30 | 25 | Irina Falconi v Valentini Grammatikopoulou | 6-2,6-3 | |
| WTA Moszkva | 10/13 12:40 | 46 | Giulia Gatto Monticone v Valentini Grammatikopoulou | 6-3,5-7,7-6 | |
| WTA Moszkva | 10/12 16:05 | 45 | [212] Elitsa Kostova v Valentini Grammatikopoulou [230] | 3-6,4-6 | |
| ITF W60 Caldas da Rainha | 09/25 19:20 | 25 | [115] Kaia Kanepi v Valentini Grammatikopoulou [232] | 7-5,6-1 | |
| ITF W25 Podgorica | 09/20 09:00 | 27 | [366] Amina Anshba v Valentini Grammatikopoulou [228] | 7-5,7-6 | |
| ITF W25 Podgorica | 09/19 10:00 | 26 | [399] Anastasia Detiuc v Valentini Grammatikopoulou [228] | 6-4,2-6,6-7 | |
| ITF W25 Podgorica | 09/18 11:00 | 25 | [491] Nika Radisic v Valentini Grammatikopoulou [228] | 4-6,1-6 | |
| ITF W25 Frydek Mistek | 09/11 13:15 | 25 | [297] Katharina Gerlach v Valentini Grammatikopoulou [237] | 6-0,6-2 | |
| ITF W25 Trieste | 09/06 09:00 | 27 | [472] Lucrezia Stefanini v Valentini Grammatikopoulou [220] | 6-1,6-0 | |
| ITF W25 Trieste | 09/05 08:15 | 26 | [479] Camilla Rosatello v Valentini Grammatikopoulou [220] | 4-6,5-7 | |
| ITF W25 Trieste | 09/04 07:00 | 25 | Lisa Ponomar v Valentini Grammatikopoulou | 2-6,0-6 | |
| US Open - nők | 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 10:30 | 25 | Valentini Gram'lou v Eva Vedder | 2-6,3-6 | |
| Wimbledon - nők | 06/25 16:35 | 44 | [194] Valentini Grammatikopoulou v Kaja Juvan [125] | 4-6,6-3,8-10 | |
| ITF W100 Ilkley | 06/18 12:15 | 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 - nők | 05/24 11:15 | 46 | [193] Valentini Grammatikopoulou v Varvara Lepchenko [130] | 2-6,2-6 | |
| French Open - nők | 05/23 09:45 | 45 | [105] Heather Watson v Valentini Grammatikopoulou [193] | 5-7,7-6,6-7 | |
| French Open - nők | 05/22 08:00 | 44 | [193] Valentini Grammatikopoulou v Kimberly Birrell [158] | 6-2,3-6,6-4 |