Stadium: Court 2 Round: 24 Ground: Clay
| ITF - W60 Berkeley | 2019/07/19 00:00 | Hailey Baptiste v Caroline Dolehide | 4-6,4-6 |
| WTA - Charleston | 2021/04/04 16:35 | Caroline Dolehide v Storm Hunter | 6-2,4-6,6-7 |
| WTA - Charleston | 2021/04/03 15:40 | Caroline Dolehide v Mirjam Bjorklund | 6-4,6-3 |
| WTA - Miami | 2021/03/22 21:40 | Timea Babos v Caroline Dolehide | 4-6,6-2,6-2 |
| WTA - Monterrey | 2021/03/15 21:10 | Caroline Dolehide v Viktoria Hruncakova | 3-6,1-6 |
| WTA - Guadalajara | 2021/03/10 01:00 | Eugenie Bouchard v Caroline Dolehide | 3-6,6-1,6-3 |
| WTA - Guadalajara | 2021/03/07 20:00 | Olga Govortsova v Caroline Dolehide | 6-7,7-5,6-7 |
| WTA - Guadalajara | 2021/03/06 22:00 | Ellen Perez v Caroline Dolehide | 3-6,7-5,4-6 |
| ITF - W25 Boca Raton | 2021/02/25 15:50 | Maria Camila Osorio v Caroline Dolehide | 6-3,7-6 |
| WTA - Miami | 2021/03/24 22:55 | Hailey Baptiste v Kristina Kucova | 4-6,6-2,5-7 |
| WTA - Miami | 2021/03/23 17:10 | Hailey Baptiste v Greet Minnen | 6-3,6-4 |
| WTA - Miami | 2021/03/22 19:15 | Misaki Doi v Hailey Baptiste | 6-1,0-6,6-7 |
| ITF - W25 Boca Raton | 2021/02/27 17:35 | Hailey Baptiste v Varvara Lepchenko | 3-6,7-6,2-6 |
| ITF - W25 Boca Raton | 2021/02/26 19:05 | Tereza Mrdeza v Hailey Baptiste | 6-3,2-6,2-6 |
| ITF - W25 Boca Raton | 2021/02/25 18:05 | Robin Montgomery v Hailey Baptiste | 3-6,3-6 |
| ITF - W25 Boca Raton | 2021/02/23 20:10 | Hailey Baptiste v Varvara Flink | 6-1,4-6,7-6 |
| ITF - W25 Orlando | 2021/02/17 23:05 | Hailey Baptiste v Renata Zarazua | 7-5,5-7,3-6 |