Stadium: Court 9 Round: 25 Ground: Hardcourt outdoor
| ITF W60 Brescia | 2023/06/01 10:00 | Louisa Chirico v Hailey Baptiste | 6-7,7-6,6-4 |
| ITF W25 Boca Raton | 2023/04/14 15:00 | Hailey Baptiste v Louisa Chirico | 6-4,2-6,7-5 |
| ITF W100 Palm Harbor | 2022/04/13 17:00 | Hailey Baptiste v Louisa Chirico | 3-6,3-6 |
| ITF W25 Plantation | 2019/01/25 15:00 | Hailey Baptiste v Louisa Chirico | 7-6,6-4 |
| ITF Women Florence | 2018/10/17 19:50 | Hailey Baptiste v Louisa Chirico | 3-6,6-4,6-7 |
| ITF W60 Templeton | 2023/09/28 21:05 | McCartney Kessler v Hailey Baptiste | 3-6,6-3,6-1 |
| ITF W60 Templeton | 2023/09/28 01:00 | Veronika Miroshnichenko v Hailey Baptiste | 6-7,6-1,4-6 |
| WTA Guadalajara | 2023/09/20 17:00 | Hailey Baptiste v Caroline Garcia | 5-7,4-6 |
| WTA Guadalajara | 2023/09/18 18:30 | Karolina Pliskova v Hailey Baptiste | 6-7,7-5,6-7 |
| WTA Guadalajara | 2023/09/17 18:50 | Hailey Baptiste v Lya Fernandez | 6-2,6-1 |
| WTA San Diego | 2023/09/10 22:20 | Magdalena Frech v Hailey Baptiste | 6-4,6-7,6-4 |
| WTA San Diego | 2023/09/10 02:25 | Victoria Hu v Hailey Baptiste | 4-6,0-6 |
| US Open Women | 2023/08/23 15:00 | Diana Shnaider v Hailey Baptiste | 6-3,6-4 |
| ITF W60 Rancho Santa Fe | 2023/10/13 19:45 | Louisa Chirico v Yulia Starodubtsewa | 6-4,3-6,4-6 |
| ITF W60 Rancho Santa Fe | 2023/10/12 17:00 | Louisa Chirico v Makenna Jones | 6-3,7-5 |
| ITF W60 Rancho Santa Fe | 2023/10/11 20:50 | Louisa Chirico v Paris Corley | 6-0,6-3 |
| ITF W60 Templeton | 2023/09/28 19:00 | Louisa Chirico v Ann Li | 5-7,2-6 |
| WTA Guadalajara | 2023/09/17 17:00 | Louisa Chirico v Jasmine Paolini | 0-6,6-7 |
| WTA San Diego | 2023/09/12 18:30 | Louisa Chirico v Danielle Rose Collins | 5-7,0-6 |
| WTA San Diego | 2023/09/10 18:00 | Renata Zarazua v Louisa Chirico | 3-6,6-3,4-6 |
| WTA San Diego | 2023/09/09 17:00 | Louisa Chirico v Caroline Dolehide | 7-6,6-2 |