Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| UTR Pro Florida Women | 2023/06/04 13:00 | Samantha Crawford v Gabriella Broadfoot | 6-4,6-1 |
| UTR Pro Florida Women | 2023/06/03 13:00 | Samantha Crawford v Kinaa Graham | 6-3,6-5 |
| UTR Pro Florida Women | 2023/06/02 15:00 | Samantha Crawford v Ichino Horikawa | 6-1,6-4 |
| UTR Pro Florida Women | 2023/05/31 16:30 | Samantha Crawford v Annabelle Davis | 6-1,6-4 |
| UTR Pro Florida Women | 2023/05/30 15:00 | Samantha Crawford v Jennifer Jackson | 6-2,6-0 |
| UTR Pro Florida Women | 2023/05/29 17:20 | Kathryn Treiber v Samantha Crawford | 0-6,1-6 |
| ITF W25 Orlando | 2023/05/11 13:30 | Dalayna Hewitt v Samantha Crawford | 3-6,6-3,7-5 |
| ITF W25 Orlando | 2023/05/10 16:10 | Samantha Crawford v Seone Mendez | 6-1,6-3 |
| ITF W15 Rancho Santa Fe | 2023/05/30 19:00 | Alicia Herrero Linana v Esther Vyrlan | 7-5,6-1 |
| ITF W25 Orlando | 2023/05/08 15:00 | Anna Gold v Esther Vyrlan | 6-3,7-6 |
| ITF W25 Zephyrhills | 2023/04/17 18:00 | Sophia Webster v Esther Vyrlan | 7-6,6-4 |
| ITF W60 Arcadia | 2023/03/01 23:45 | Ganna Poznikhirenko v Esther Vyrlan | 6-1,4-6,6-1 |
| ITF W60 Arcadia | 2023/02/28 20:00 | Esther Vyrlan v Maika M Adair | 6-1,6-1 |
| ITF W25 Santo Domingo | 2023/02/20 16:15 | Bianca Jolie Fernandez v Esther Vyrlan | 7-5,6-1 |
| ITF W25 Santo Domingo Qual | 2023/02/19 19:00 | Esther Vyrlan v Mia Popovic | 6-2,7-5 |
| ITF W25 Malibu | 2023/01/02 17:00 | Carolyn Campana v Esther Vyrlan | 6-2,6-2 |