Stadium: Court 1 Round: 27 Ground: Hardcourt indoor
| ITF W60 Toronto | 2019/10/31 17:15 | Kirsten Flipkens v Fanny Stollar | 6-2,6-2 |
| ITF W60 Toronto | 2019/10/30 18:40 | Kirsten Flipkens v Ariana Arseneault | 6-2,6-1 |
| WTA Moscow | 2019/10/18 11:25 | Kirsten Flipkens v Belinda Bencic | 6-7,1-6 |
| WTA Moscow | 2019/10/16 11:35 | Dayana Yastremska v Kirsten Flipkens | 3-6,6-3,3-6 |
| WTA Moscow | 2019/10/15 09:30 | Kirsten Flipkens v Natalia Vikhlyantseva | 6-3,6-2 |
| WTA Moscow | 2019/10/14 09:20 | Kirsten Flipkens v Gabriela Dabrowski | 6-1,6-4 |
| WTA Moscow | 2019/10/13 09:00 | Kirsten Flipkens v Ludmilla Samsonova | 7-5,6-4 |
| WTA Moscow | 2019/10/12 08:00 | Kirsten Flipkens v Anastasia Gasanova | 6-1,6-2 |
| ITF W60 Toronto | 2019/10/31 16:55 | Naomi Broady v Elitsa Kostova | 3-6,3-6 |
| ITF W60 Toronto | 2019/10/30 13:50 | Melodie Collard v Elitsa Kostova | 2-6,6-4,1-6 |
| ITF W25 Istanbul | 2019/10/23 09:55 | Elitsa Kostova v Anna Kubareva | 6-7,6-2,5-7 |
| ITF W25 Istanbul | 2019/10/22 12:40 | Elitsa Kostova v Berfu Cengiz | 7-5,6-0 |
| WTA Moscow | 2019/10/12 16:05 | Elitsa Kostova v Valentini Grammatikopoulou | 3-6,4-6 |
| ITF W25 Santa Margherita | 2019/10/05 12:00 | Elitsa Kostova v Teliana Pereira | 5-7,4-6 |
| ITF W25 Santa Margherita | 2019/10/04 12:00 | Carolina Alves v Elitsa Kostova | 3-6,4-6 |
| ITF W25 Santa Margherita | 2019/10/03 12:00 | Anastasia Detiuc v Elitsa Kostova | 4-6,6-4,1-6 |