[83] Katie Boulter 6-3,4-6,6-3 Valentini Grammatikopoulou [171] 2019-02-07 16:30
Home History
| 2019 Fed Cup | 2019/02/06 16:30 | Katie Boulter v Kaja Juvan | 6-4,6-2 |
| WTA St. Petersburg | 2019/01/30 10:00 | Katie Boulter v Ekaterina Alexandrova | 5-7,6-4,1-6 |
| WTA St. Petersburg | 2019/01/28 08:00 | Ysaline Bonaventure v Katie Boulter | 6-7,6-4,6-2 |
| WTA St. Petersburg | 2019/01/27 09:20 | Katarina Zavatska v Katie Boulter | 7-6,1-6,5-7 |
| WTA St. Petersburg | 2019/01/26 11:25 | Katie Boulter v Bernarda Pera | 7-6,3-6,6-1 |
| Australian Open Women | 2019/01/16 05:40 | Katie Boulter v Aryna Sabalenka | 3-6,4-6 |
| Australian Open Women | 2019/01/14 00:00 | Katie Boulter v Ekaterina Makarova | 6-0,4-6,7-6 |
| WTA Hobart | 2019/01/05 02:20 | Greet Minnen v Katie Boulter | 6-3,3-6,6-1 |
Away History
| 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 Women | 2019/01/10 06:55 | Bianca Andreescu v Valentini Grammatikopoulou | 6-4,6-1 |
| Australian Open Women | 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 Hong Kong | 2019/01/02 06:15 | Valentini Grammatikopoulou v Ho Ching Wu | 6-1,6-4 |
| ITF Women Dubai | 2018/12/10 09:40 | Mandy Minella v Valentini Grammatikopoulou | 6-1,6-4 |