Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| WTA Houston | 2019/11/11 16:00 | Hailey Baptiste v Elitsa Kostova | 6-2,6-4 |
| ITF W60 Asuncion | 2019/10/29 22:20 | Hailey Baptiste v Lara Escauriza | 5-7,4-6 |
| ITF W25 Hilton Head Island | 2019/10/09 17:55 | Hailey Baptiste v Emiliana Arango | 4-6,6-7 |
| ITF W60 Charleston | 2019/10/03 16:15 | Hailey Baptiste v Grace Min | 3-6,6-2,5-7 |
| ITF W60 Charleston | 2019/10/02 19:40 | Hailey Baptiste v Sophie Chang | 6-4,6-3 |
| ITF W60 Templeton | 2019/09/26 18:25 | Emina Bektas v Hailey Baptiste | 7-5,4-6,6-4 |
| ITF W60 Templeton | 2019/09/24 20:10 | Marcela Zacarias v Hailey Baptiste | 5-7,7-6,2-6 |
| US Open Women | 2019/08/22 17:40 | Hailey Baptiste v Harriet Dart | 5-7,4-6 |
| ITF W60 Las Vegas | 2019/11/06 18:45 | Kirsten Flipkens v Alycia Parks | 4-6,6-3,5-7 |
| ITF W60 Toronto | 2019/11/03 17:00 | Kirsten Flipkens v Francesca Di Lorenzo | 6-7,4-6 |
| ITF W60 Toronto | 2019/11/02 17:30 | Kirsten Flipkens v Samantha Murray | 2-6,6-2,6-3 |
| ITF W60 Toronto | 2019/11/01 18:05 | Kirsten Flipkens v Elitsa Kostova | 6-3,6-2 |
| 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 |