Stadium: Center Court Round: 27 Ground: Hardcourt outdoor
| ITF W25 Boca Raton | 2021/02/25 18:05 | Robin Montgomery v Hailey Baptiste | 3-6,3-6 |
| WTA Puerto Vallarta | 2024/02/22 02:30 | Hailey Baptiste v Iryna Shymanovich | 6-0,6-1 |
| WTA Puerto Vallarta | 2024/02/20 18:00 | Hailey Baptiste v Martina Capurro Taborda | 6-1,6-3 |
| ITF W50 Morelia | 2024/02/17 21:05 | Hailey Baptiste v Jessica Bouzas Maneiro | 7-6,1-6,6-7 |
| ITF W50 Morelia | 2024/02/17 16:30 | Hailey Baptiste v Rebecca Marino | 7-5,6-1 |
| ITF W50 Morelia | 2024/02/16 01:30 | Hailey Baptiste v Natalija Stevanovic | 4-6,6-4,6-3 |
| ITF W50 Morelia | 2024/02/14 18:30 | Hailey Baptiste v Jessica Failla | 6-3,2-6,6-4 |
| ITF W50 Morelia | 2024/02/13 19:00 | Hailey Baptiste v Maria Jose Portillo Ramirez | 6-1,6-0 |
| ITF W100 Irapuato | 2024/02/07 19:00 | Iryna Shymanovich v Hailey Baptiste | 6-4,6-3 |
| 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 Puerto Vallarta | 2024/02/19 18:00 | Robin Montgomery v Elvina Kalieva | 6-2,6-4 |
| ITF W75 Rome (GA) | 2024/02/02 18:05 | McCartney Kessler v Robin Montgomery | 7-6,6-3 |
| ITF W75 Rome (GA) | 2024/02/01 17:40 | Louisa Chirico v Robin Montgomery | 2-6,1-6 |
| ITF W75 Rome (GA) | 2024/01/30 18:45 | Clervie Ngounoue v Robin Montgomery | 5-7,4-6 |
| ITF W75 Vero Beach | 2024/01/24 17:00 | Gabriela Lee v Robin Montgomery | 6-2,6-0 |
| ITF W35 Naples | 2024/01/20 15:55 | Robin Montgomery v Leonie Kung | 3-6,6-1,5-7 |