Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| WTA Taipei | 2019/11/12 05:30 | Kaja Juvan v Emily Webley-Smith | 6-1,6-2 |
| WTA Taipei | 2019/11/11 04:35 | Emily Webley-Smith v Yana Sizikova | 6-2,6-2 |
| WTA Taipei | 2019/11/10 05:40 | Emily Webley-Smith v I-Hsuan Cho | 6-4,6-1 |
| ITF W60 Liuzhou | 2019/10/28 10:10 | Urszula Radwanska v Emily Webley-Smith | 6-0,6-2 |
| ITF W25 Nanning | 2019/10/21 03:30 | Ying Zhang v Emily Webley-Smith | 6-4,0-6,10-5 |
| ITF W100 Suzhou | 2019/10/17 03:00 | Peangtarn Plipuech v Emily Webley-Smith | 7-6,6-4 |
| ITF W100 Suzhou | 2019/10/16 03:25 | Emily Webley-Smith v Yi Yuan | 6-2,6-1 |
| ITF W100 Suzhou | 2019/10/15 03:45 | Qianhui Tang v Emily Webley-Smith | 6-7,2-6 |
| ITF W25 Gwalior | 2019/11/14 06:30 | Gergana Topalova v Karman Kaur Thandi | 2-6,4-6 |
| ITF W25 Gwalior | 2019/11/13 05:50 | Valeriya Strakhova v Gergana Topalova | 6-3,6-7,0-6 |
| ITF W25 Istanbul | 2019/10/21 07:00 | Lina Gjorcheska v Gergana Topalova | 6-4,6-2 |
| ITF W15 Antalya | 2019/10/15 07:00 | Eliessa Vanlangendonck v Gergana Topalova | 7-5,1-6,6-4 |
| ITF W15 Antalya | 2019/10/12 07:30 | Romy Koelzer v Gergana Topalova | 6-1,6-1 |
| ITF W15 Antalya | 2019/10/10 07:00 | Karola Patricia Bejenaru v Gergana Topalova | 6-4,0-6,2-6 |
| ITF W15 Antalya | 2019/10/09 09:00 | Zeynep Sena Sarioglan v Gergana Topalova | 3-6,0-6 |
| ITF W15 Sozopol | 2019/10/02 08:50 | Gergana Topalova v Ekaterina Reyngold | 2-6,0-6 |