Stadium: Cancha 8 Round: 26 Ground: Clay
| WTA - Indian Wells | 2024/03/07 21:50 | Robin Montgomery v Hailey Baptiste | 2-6,6-4,1-6 |
| WTA - Puerto Vallarta | 2024/02/24 02:45 | Hailey Baptiste v Robin Montgomery | 4-6,6-1,6-2 |
| ITF W25 - Boca Raton | 2021/02/25 18:05 | Robin Montgomery v Hailey Baptiste | 3-6,3-6 |
| WTA - San Luis Potosi | 2024/03/25 23:35 | Astra Sharma v Robin Montgomery | 3-6,4-6 |
| WTA - Miami | 2024/03/17 18:30 | Laura Siegemund v Robin Montgomery | 6-0,6-0 |
| WTA - Indian Wells | 2024/03/07 21:50 | Robin Montgomery v Hailey Baptiste | 2-6,6-4,1-6 |
| WTA - Indian Wells | 2024/03/05 22:00 | Storm Hunter v Robin Montgomery | 6-3,3-6,4-6 |
| WTA - Indian Wells | 2024/03/04 00:50 | Robin Montgomery v Marina Bassols Ribera | 6-4,6-4 |
| WTA - Puerto Vallarta | 2024/02/24 02:45 | Hailey Baptiste v Robin Montgomery | 4-6,6-1,6-2 |
| WTA - Puerto Vallarta | 2024/02/22 00:50 | Robin Montgomery v Renata Zarazua | 6-1,6-4 |
| WTA - Puerto Vallarta | 2024/02/20 21:35 | Robin Montgomery v Solana Sierra | 6-1,7-5 |
| WTA - San Luis Potosi | 2024/03/25 21:55 | Maria F Navarro Oliva v Hailey Baptiste | 4-6,1-6 |
| WTA - Miami | 2024/03/19 15:00 | Xinyu Wang v Hailey Baptiste | 7-6,6-3 |
| WTA - Indian Wells | 2024/03/09 04:30 | Madison Keys v Hailey Baptiste | 6-4,4-6,7-6 |
| WTA - Indian Wells | 2024/03/07 21:50 | Robin Montgomery v Hailey Baptiste | 2-6,6-4,1-6 |
| WTA - Indian Wells | 2024/03/05 22:00 | Clara Tauson v Hailey Baptiste | 6-7,6-7 |
| WTA - Indian Wells | 2024/03/04 21:15 | Daria Snigur v Hailey Baptiste | 2-6,3-6 |
| WTA - Puerto Vallarta | 2024/02/25 01:35 | Hailey Baptiste v McCartney Kessler | 4-6,4-6 |
| WTA - Puerto Vallarta | 2024/02/24 02:45 | Hailey Baptiste v Robin Montgomery | 4-6,6-1,6-2 |