Stadium: Court 8 Round: 44 Ground: Hardcourt outdoor
| Vancouver, Simples W-ITF-CAN-02A | 2019/08/16 19:35 | Maddison Inglis v Heather Watson | 3-6,2-6 |
| Vancouver, Simples W-ITF-CAN-02A | 2019/08/15 18:35 | Maddison Inglis v Muhammad, Asia | 2-6,7-6,6-4 |
| Granby, Simples W-ITF-CAN-05A | 2019/07/26 23:00 | Fernandez, Leylah Annie v Maddison Inglis | 6-3,6-4 |
| Granby, Simples W-ITF-CAN-05A | 2019/07/25 15:35 | Halbauer, Elizabeth v Maddison Inglis | 7-6,6-7,4-6 |
| Granby, Simples W-ITF-CAN-05A | 2019/07/24 20:40 | Ghitescu, Andreea v Maddison Inglis | 4-6,5-7 |
| ITF W25 Saskatoon | 2019/07/14 17:00 | Katherine Sebov v Maddison Inglis | 4-6,6-2,4-6 |
| ITF W25 Saskatoon | 2019/07/13 19:20 | Haruka Kaji v Maddison Inglis | 6-3,6-7,2-6 |
| ITF W25 Saskatoon | 2019/07/12 19:00 | Carol Zhao v Maddison Inglis | 1-6,1-6 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/10 10:30 | Valentini Grammatikopoulou v Murray Sharan, S. | 4-6,2-6 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/09 10:30 | Ekani, Irys v Valentini Grammatikopoulou | 6-3,4-6,2-6 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/08 09:00 | Yuriko Lily Miyazaki v Valentini Grammatikopoulou | 3-6,6-4,6-7 |
| Chiswick, Singles W-ITF-GBR-09A | 2019/08/06 11:00 | Ali Collins v Valentini Grammatikopoulou | 1-6,6-2,0-6 |
| WTA Lausanne | 2019/07/13 09:55 | Wuarin, Pauline v Valentini Grammatikopoulou | 1-6,6-4,6-3 |
| ITF W60 Versmold | 2019/07/11 11:00 | Louisa Chirico v Valentini Grammatikopoulou | 6-4,2-6,7-6 |
| ITF W60 Versmold | 2019/07/10 12:30 | Shoshyna, Anastasiya v Valentini Grammatikopoulou | 2-6,2-6 |
| ITF W25 Den Haag | 2019/07/02 10:30 | Valentini Grammatikopoulou v Eva Vedder | 2-6,3-6 |