| ITF Women Shenzhen Qual | 03/10 03:10 | 45 | Valentini Grammatikopoulou v Ling Zhang | 6-3,6-3 | |
| ITF Women Zhuhai | 03/07 04:45 | 25 | Deborah Chiesa v Valentini Grammatikopoulou | 6-1,6-2 | |
| ITF Women Altenkirchen | 02/21 16:25 | 25 | Lena Rueffer v Valentini Grammatikopoulou | 7-6,6-2 | |
| ITF Women Loughborough | 02/08 11:25 | 26 | Jesika Maleckova v Valentini Grammatikopoulou | 7-6,6-3 | |
| ITF Women Loughborough | 02/07 12:15 | 25 | Petra Krejsova v Valentini Grammatikopoulou | 5-7,1-6 | |
| ITF Women Glasgow | 01/31 10:00 | 25 | Valentini Grammatikopoulou v Freya Christie | 4-6,3-6 | |
| Australian Open Women Qual | 01/13 09:10 | 45 | Lin Zhu v Valentini Gramma'poulou | 4-6,6-2,7-5 | |
| Australian Open Women Qual | 01/11 03:30 | 44 | Valentini Gramma'poulou v Ellen Perez | 6-3,4-6,6-2 | |
| ITF Women Playford | 01/04 23:30 | 27 | Alexandra Bozovic v Valentini Gramma'poulou | 7-6,4-6,6-4 | |
| ITF Women Playford | 01/04 05:20 | 26 | Valentini Gramma'poulou v Jil Teichmann | 7-6,6-3 | |
| ITF Women Playford | 01/03 06:00 | 25 | Valentini Gramma'poulou v Marta Kostyuk | 7-5,6-3 | |
| ITF Women Dakar | 11/19 15:30 | 29 | [330] Chanel Simmonds v Valentini Grammatikopoulou [212] | 0-6,6-7 | |
| ITF Women Dakar | 11/18 11:00 | 28 | [251] Georgina Garcia-Perez v Valentini Grammatikopoulou [212] | 6-3,6-7,6-7 | |
| ITF Women Dakar | 11/17 13:00 | 27 | [301] Katie Swan v Valentini Grammatikopoulou [212] | 7-5,4-6,4-6 | |
| ITF Women Dakar | 11/16 13:00 | 26 | Polina Golubovskaya v Valentini Grammatikopoulou | 6-4,0-6,0-6 | |
| ITF Women Dakar | 11/13 11:40 | 25 | Barbora Miklova v Valentini Grammatikopoulou | 4-6,3-6 | |
| WTA Moscow Qual | 10/15 09:00 | 46 | Polina Monova v Valentini Grammatikopoulou | 7-6,6-4 | |
| WTA Moscow Qual | 10/14 09:30 | 45 | Margarita Gasparyan v Valentini Grammatikopoulou | 6-4,5-7,5-7 | |
| WTA Hongkong | 10/09 07:00 | 25 | [207] Valentini Grammatikopoulou v Nicole Gibbs [114] | 6-4,2-6,5-7 | |
| WTA Hong Kong Qual | 10/08 04:00 | 46 | [208] Valentini Grammatikopoulou v Junri Namigata [241] | 4-6,6-4,6-1 | |
| WTA Hong Kong Qual | 10/07 05:05 | 45 | Valentini Grammatikopoulou v Hong Yi Cody Wong | 6-4,6-4 | |
| WTA Tashkent Qual | 09/23 09:20 | 26 | [201] Valentini Grammatikopoulou v Lizette Cabrera [153] | 3-6,6-2,3-6 | |
| ITF Women St. Petersburg | 09/21 11:50 | 27 | [178] Anhelina Kalinina v Valentini Gramma'poulou [201] | 3-6,6-4,6-2 | |
| ITF Women St. Petersburg | 09/20 12:10 | 26 | [201] Valentini Gramma'poulou v Pauline Parmentier [100] | 6-1,6-0 | |
| ITF Women St. Petersburg | 09/18 10:40 | 25 | [469] Margarita Lazareva v Valentini Gramma'poulou [201] | 1-6,1-6 | |
| ITF Women Sofia | 09/07 08:20 | 26 | [191] Valentini Grammatikopoulou v Jaqueline Adina Cristian [334] | 2-6,3-6 | |
| ITF Women Sofia | 09/06 07:00 | 25 | [191] Valentini Grammatikopoulou v Cristina Dinu [401] | 6-4,5-7,6-2 | |
| US Open Women Qual | 08/23 16:45 | 44 | [122] Tereza Martincova v Valentini Grammatikopoulou [176] | 4-6,7-6,6-4 | |
| ITF Women Vancouver Qual | 08/15 17:00 | 54 | [174] Valentini Gram'lou v Priscilla Hon [354] | 2-6,6-7 | |
| ITF Women Vancouver Qual | 08/14 16:00 | 54 | [174] Valentini Gram'lou v Nicole Melichar [51] | 6-4,1-6,6-4 |