Stadium: Stadium Round: 26 Ground: Clay
| WTA Charleston | 2022/04/02 15:55 | Caroline Dolehide v Louisa Chirico | 3-6,6-3,3-6 |
| ITF - Charleston W100 | 2019/05/01 18:35 | Louisa Chirico v Caroline Dolehide | 6-0,6-4 |
| ITF - Bonita Springs W100 | 2023/05/03 19:10 | Noelia Zeballos v Louisa Chirico | 3-6,3-6 |
| ITF - Charlottesville W60 | 2023/04/26 19:30 | Maria Mateas v Louisa Chirico | 6-4,6-3 |
| ITF - Charleston W100 | 2023/04/19 14:00 | Louisa Chirico v Elizabeth Mandlik | 1-6,3-5 |
| ITF - Boca Raton W25 | 2023/04/14 15:00 | Hailey Baptiste v Louisa Chirico | 6-4,2-6,7-5 |
| ITF - Boca Raton W25 | 2023/04/12 13:00 | Olga Govortsova v Louisa Chirico | 0-6,3-6 |
| WTA Charleston | 2023/04/03 21:55 | Sloane Stephens v Louisa Chirico | 3-6,6-1,6-2 |
| WTA Charleston | 2023/04/02 14:00 | Elvina Kalieva v Louisa Chirico | 4-6,1-6 |
| WTA Charleston | 2023/04/01 15:35 | Sophie Chang v Louisa Chirico | 6-7,3-6 |
| ITF - Bonita Springs W100 | 2023/05/03 21:25 | Yulia Starodubtsewa v Caroline Dolehide | 4-6,4-6 |
| ITF - Charlottesville W60 | 2023/04/29 17:25 | Ashlyn Krueger v Caroline Dolehide | 6-4,7-5 |
| ITF - Charlottesville W60 | 2023/04/28 17:30 | Renata Zarazua v Caroline Dolehide | 3-6,3-6 |
| ITF - Charlottesville W60 | 2023/04/27 15:50 | Marcela Zacarias v Caroline Dolehide | 0-6,2-6 |
| ITF - Charlottesville W60 | 2023/04/26 13:50 | Liv Hovde v Caroline Dolehide | 6-3,4-6,1-6 |
| ITF - Charleston W100 | 2023/04/22 17:30 | Peyton Stearns v Caroline Dolehide | 6-2,7-5 |
| ITF - Charleston W100 | 2023/04/21 17:10 | Nao Hibino v Caroline Dolehide | 2-6,3-6 |
| ITF - Charleston W100 | 2023/04/20 18:05 | Taylor Ng v Caroline Dolehide | 5-7,6-3,2-6 |