stadio: Court 8 Round: 29 Ground: Clay
| WTA Charleston | 2021/04/06 17:25 | Caroline Dolehide v Hailey Baptiste | 3-6,3-6 |
| ITF W60 Berkeley | 2019/07/19 00:00 | Hailey Baptiste v Caroline Dolehide | 4-6,4-6 |
| ITF W25 Boca Raton | 2023/04/15 18:15 | Caroline Dolehide v Gabriela Lee | 6-2,6-2 |
| ITF W25 Boca Raton | 2023/04/15 13:00 | Emma Navarro v Caroline Dolehide | 2-6,6-3,2-6 |
| ITF W25 Boca Raton | 2023/04/14 13:00 | Sophie Chang v Caroline Dolehide | 3-6,3-6 |
| ITF W25 Boca Raton | 2023/04/13 15:40 | Gabriela Ce v Caroline Dolehide | 1-6,0-6 |
| WTA Charleston | 2023/04/06 16:35 | Caroline Dolehide v Ons Jabeur | 3-6,5-7 |
| WTA Charleston | 2023/04/05 16:05 | Linda Fruhvirtova v Caroline Dolehide | 2-6,7-5,3-6 |
| WTA Charleston | 2023/04/04 16:55 | Caroline Dolehide v Sabine Lisicki | 6-4,6-4 |
| WTA Indian Wells | 2023/03/07 20:20 | Rebecca Peterson v Caroline Dolehide | 7-5,7-6 |
| ITF W25 Boca Raton | 2023/04/15 17:00 | Hailey Baptiste v Sachia Vickery | 6-4,6-2 |
| ITF W25 Boca Raton | 2023/04/15 13:00 | Yulia Starodubtsewa v Hailey Baptiste | 3-6,0-6 |
| ITF W25 Boca Raton | 2023/04/14 15:00 | Hailey Baptiste v Louisa Chirico | 6-4,2-6,7-5 |
| ITF W25 Boca Raton | 2023/04/13 13:50 | Hailey Baptiste v Jamie Loeb | 6-1,6-4 |
| WTA Charleston | 2023/04/05 17:05 | Hailey Baptiste v Madison Keys | 1-6,2-6 |
| WTA Charleston | 2023/04/04 18:35 | Xiyu Wang v Hailey Baptiste | 3-6,3-6 |
| WTA Charleston | 2023/04/02 16:40 | Hailey Baptiste v Heather Watson | 7-5,6-3 |
| WTA Charleston | 2023/04/01 20:45 | Hailey Baptiste v Marcela Zacarias | 6-2,6-1 |