| ITF Women Vancouver Qual | 08/14 16:00 | 54 | [174] Grammatikopoulou, Valentini v Melichar, Nicole [51] | 6-4,1-6,6-4 | |
| ITF Women Landisville | 08/09 14:00 | 25 | Osaka, Mari v Valentini Grammatikopoulou | 5-7,7-5,6-2 | |
| WTA Washington | 08/02 18:00 | 25 | Lisicki, Sabine v Valentini Grammatikopoulou | 7-6,7-6 | |
| Washington, USA, Qualifying | 07/30 19:00 | 46 | Xu, Shilin v Grammatikopoulou, Valentini | 3-6,3-6 | |
| Washington, USA, Qualifying | 07/30 15:20 | 45 | Morra, Cameron v Grammatikopoulou, Valentini | 4-6,6-4,2-6 | |
| WTA Gstaad Qual | 07/16 09:00 | 46 | [161] Smitkova, Tereza v Valentini Grammatikopoulou [199] | 6-7,7-5,6-1 | |
| WTA Gstaad Qual | 07/15 11:00 | 45 | [141] Lister, Cornelia v Valentini Grammatikopoulou [199] | 3-6,3-6 | |
| ITF Women Middelburg | 07/09 11:00 | 29 | [157] Arantxa Rus v Valentini Grammatikopoulou [199] | 3-6,6-2,6-3 | |
| ITF Women Middelburg | 07/08 10:00 | 28 | [264] Dejana Radanovic v Valentini Grammatikopoulou [199] | 6-4,4-6,6-7 | |
| ITF Women Middelburg | 07/07 11:35 | 27 | Zoe Hives v Valentini Grammatikopoulou | 4-6,1-6 | |
| ITF Women Middelburg | 07/06 12:45 | 26 | [435] Scholsen, Helene v Valentini Grammatikopoulou [199] | 4-6,3-6 | |
| ITF Women Middelburg | 07/04 17:30 | 25 | [491] Naiktha Bains v Valentini Grammatikopoulou [199] | 6-7,4-6 | |
| Wimbledon Women Qual | 06/27 11:40 | 44 | [176] Soylu, Ipek v Valentini Grammatikopoulou [198] | 6-4,6-3 | |
| ITF Women Ilkley Qual | 06/19 13:15 | 54 | [84] Dzalamidze, Natela v Valentini Grammatikopoulou [163] | 6-4,7-5 | |
| ITF Women Ilkley Qual | 06/18 15:00 | 54 | [480] Naiktha Bains v Valentini Grammatikopoulou [159] | 2-6,3-6 | |
| Fed Cup, Matchs en Doubles | 06/17 07:20 | - | Valentini Grammatikopoulou v Suomalainen, Piia | 7-5,6-1 | |
| Fed Cup, Matchs en Doubles | 06/14 08:55 | - | Valentini Grammatikopoulou v Genovese, Elaine | 4-6,7-5,6-2 | |
| French Open Women Qual | 05/25 11:25 | 45 | [168] Valentini Grammatikopoulou v Jil Teichmann [153] | 0-6,2-6 | |
| French Open Women Qual | 05/23 10:40 | 44 | [168] Valentini Grammatikopoulou v Lizette Cabrera [174] | 6-4,6-3 | |
| ITF Women Saint Gaudens | 05/20 12:30 | 28 | [183] Valentini Grammatikopoulou v Hogenkamp, Richel [112] | 4-6,3-6 | |
| ITF Women Saint Gaudens | 05/19 11:00 | 27 | Irina Khromacheva v Valentini Grammatikopoulou | Retired | |
| ITF Women Saint Gaudens | 05/17 13:25 | 26 | [183] Valentini Grammatikopoulou v Soylu, Ipek [155] | 6-3,6-3 | |
| ITF Women Saint Gaudens | 05/16 13:45 | 25 | [220] Amandine Hesse v Valentini Grammatikopoulou [183] | 6-7,5-7 | |
| ITF Women Monzon | 05/09 11:00 | 25 | [340] Dejana Radanovic v Valentini Grammatikopoulou [183] | 7-5,7-6 | |
| ITF Women Anning | 04/27 09:00 | 27 | [187] Zarina Diyas v Valentini Grammatikopoulou [192] | 6-3,6-1 | |
| ITF Women Anning | 04/26 03:00 | 26 | [253] Cako, Jacqueline v Valentini Grammatikopoulou [192] | 4-6,6-2,1-6 | |
| ITF Women Anning | 04/24 05:15 | 25 | [207] Sawayanagi, Riko v Valentini Grammatikopoulou [196] | Retired | |
| Zhengzhou, Chine | 04/19 04:00 | 26 | [196] Grammatikopoulou, Valentini v Qiang Wang [68] | 6-4,5-7,2-6 | |
| Zhengzhou, Chine | 04/17 04:00 | 25 | [196] Grammatikopoulou, Valentini v Xu, Yi-Fan [378] | 6-1,6-3 | |
| Istanbul, Singles W-WITF-TUR-28B | 04/12 07:00 | 26 | [202] Valentini Grammatikopoulou v Basak Eraydin [335] | 1-6,2-6 |