| ITF W35 Hammamet | 04/17 08:30 | 25 | Ikumi Yamazaki v Valentini Grammatikopoulou | 6-4,7-5 | |
| Billie Jean King Cup | 04/12 09:55 | 1 | Johanne C Svendsen v Valentini Grammatikopoulou | 7-6,4-6,6-3 | |
| Billie Jean King Cup | 04/11 10:00 | 1 | [366] Daniela Vismane v Valentini Grammatikopoulou [206] | 0-6,5-7 | |
| Billie Jean King Cup | 04/10 10:15 | 1 | Valentini Grammatikopoulou v Emily Sartz-Lunde | 6-3,2-6,6-4 | |
| Billie Jean King Cup | 04/09 11:35 | 2 | [335] Mia Ristic v Valentini Grammatikopoulou [206] | 2-6,6-4,6-1 | |
| Billie Jean King Cup | 04/08 12:05 | 2 | [442] Caijsa W Hennemann v Valentini Grammatikopoulou [206] | 6-4,3-6,6-4 | |
| ITF W75 Split | 04/04 09:00 | 27 | [210] Valentini Grammatikopoulou v Panna Udvardy [161] | 1-6,6-4,4-6 | |
| ITF W75 Split | 04/03 09:00 | 26 | [210] Valentini Grammatikopoulou v Veronika Miroshnichenko [317] | 6-2,6-1 | |
| ITF W75 Split | 04/02 13:00 | 25 | [186] Carole Monnet v Valentini Grammatikopoulou [210] | 1-6,1-6 | |
| ITF W75 Croissy-Beaubourg | 03/27 10:10 | 26 | [258] Margaux Rouvroy v Valentini Grammatikopoulou [218] | 6-3,6-1 | |
| ITF W75 Croissy-Beaubourg | 03/26 13:05 | 25 | [218] Valentini Grammatikopoulou v Olivia Gadecki [149] | 4-6,7-6,7-5 | |
| ITF W35 Solarino | 03/07 10:00 | 26 | [337] Barbora Palicova v Valentini Grammatikopoulou [211] | 6-4,1-6,6-1 | |
| ITF W35 Solarino | 03/05 09:45 | 25 | Camilla Gennaro v Valentini Grammatikopoulou | 1-6,4-6 | |
| ITF W35 Helsinki | 02/28 08:00 | 25 | [217] Valentini Grammatikopoulou v Mona Barthel [285] | 5-7,3-6 | |
| ITF W35 Nakhon Si Thammarat | 02/14 03:25 | 25 | [214] Valentini Grammatikopoulou v Antonia Schmidt [497] | 3-6,6-4,6-7 | |
| WTA Mumbai | 02/03 07:05 | 14 | [206] Valentini Grammatikopoulou v Shrivalli R Bhamidipaty [374] | 3-6,2-6 | |
| WTA Hua Hin | 01/27 04:00 | 14 | [219] Valentini Grammatikopoulou v Panna Udvardy [162] | 3-6,3-6 | |
| Australian Open Women | 01/11 02:00 | 15 | [96] Dayana Yastremska v Valentini Grammatikopoulou [221] | 6-4,3-6,6-4 | |
| Australian Open Women | 01/10 00:45 | 14 | [221] Valentini Grammatikopoulou v Elvina Kalieva [199] | 7-5,6-3 | |
| WTA Montevideo | 12/04 20:30 | 25 | [364] Daria Lodikova v Valentini Grammatikopoulou [217] | 7-6,6-2 | |
| WTA Buenos Aires | 11/28 14:00 | 25 | [217] Valentini Grammatikopoulou v Ipek Oz [247] | 6-7,0-6 | |
| ITF W100 Valencia | 11/22 11:00 | 25 | [216] Valentini Grammatikopoulou v Leyre Romero Gormaz [293] | 4-6,6-1,3-6 | |
| ITF W40 Funchal | 11/15 10:55 | 25 | [217] Valentini Grammatikopoulou v Valentina Ryser [296] | 2-6,3-6 | |
| ITF W25 Monastir | 11/02 09:35 | 26 | [235] Valentini Grammatikopoulou v Alina Charaeva [496] | 2-6,3-6 | |
| ITF W25 Monastir | 11/01 13:40 | 25 | Valentini Grammatikopoulou v Nadine Keller | Cancelled | |
| ITF W25 Monastir | 11/01 13:20 | 25 | Valentini Grammatikopoulou v Tamara Curovic | 6-4,6-2 | |
| ITF W25 Sharm El Sheikh | 10/29 08:00 | 29 | Valentini Grammatikopoulou v Linda Klimovicova | 7-6,7-5 | |
| 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 |