Stadium: Court E Round: 25 Ground: Hardcourt outdoor
| 2019 Fed Cup | 2019/02/08 16:30 | Valentini Grammatikopoulou v Kaja Juvan | 7-6,5-7,6-3 |
| 2019 Fed Cup | 2019/02/07 16:30 | Katie Boulter v Valentini Grammatikopoulou | 6-3,4-6,6-3 |
| 2019 Fed Cup | 2019/02/06 16:30 | Dalma Galfi v Valentini Grammatikopoulou | 6-0,6-3 |
| WTA - St. Petersburg | 2019/01/26 18:55 | Valentini Grammatikopoulou v Jana Fett | 1-6,1-6 |
| Australian Open - Feminin | 2019/01/10 06:55 | Bianca Andreescu v Valentini Grammatikopoulou | 6-4,6-1 |
| Australian Open - Feminin | 2019/01/09 05:05 | Valentini Grammatikopoulou v Irina Maria Bara | 6-3,6-2 |
| ITF - W25 Hong Kong | 2019/01/04 03:45 | Valentini Grammatikopoulou v Barbora Stefkova | 5-7,3-6 |
| ITF - W25 Hong Kong | 2019/01/03 06:45 | Valentini Grammatikopoulou v Hiroko Kuwata | 6-4,0-6,7-6 |
| ITF W25 Nishi-Tama | 2019/03/12 03:05 | Honoka Kobayashi v Catherine Harrison | 4-6,6-1,7-10 |
| ITF W25 Nishi-Tama | 2019/03/11 06:00 | Catherine Harrison v Leylah Annie Fernandez | 6-2,6-7,12-10 |
| ITF - W25 Yokohama | 2019/03/09 04:10 | Catherine Harrison v Greet Minnen | 1-6,3-6 |
| ITF - W25 Yokohama | 2019/03/08 04:20 | Catherine Harrison v Hua-Chen Lee | 7-5,6-2 |
| ITF - W25 Yokohama | 2019/03/07 02:50 | Rutuja Bhosale v Catherine Harrison | 2-6,1-6 |
| ITF - W25 Yokohama | 2019/03/06 01:30 | Catherine Harrison v Nudnida Luangnam | 6-0,7-6 |
| ITF - W25 Yokohama | 2019/03/05 01:30 | Ji-Hee Choi v Catherine Harrison | 3-6,3-6 |
| ITF - W25 Yokohama | 2019/03/04 03:25 | Catherine Harrison v Mana Ayukawa | 6-2,7-6 |