Ground: Hardcourt indoor
| UTR Pro Winston-Salem Women | 2023/09/08 15:00 | Lucia De Santa Ana v Brooklyn Olson | 4-6,0-0 |
| UTR Pro Winston-Salem Women | 2023/09/07 18:30 | Jessie Aney v Brooklyn Olson | 6-2,6-0 |
| UTR Pro Winston-Salem Women | 2023/09/06 21:30 | Sankavi Gownder v Brooklyn Olson | 7-5,6-3 |
| UTR Pro Winston-Salem Women | 2023/09/05 23:54 | Marcella Cruz v Brooklyn Olson | 6-0,6-2 |
| UTR Pro Winston-Salem Women | 2023/09/03 19:25 | Emma Wilkins v Brooklyn Olson | 2-6,3-6 |
| UTR Pro Florida Women | 2023/06/03 14:30 | Elizabeth Ionescu v Brooklyn Olson | 6-2,4-6,6-0 |
| UTR Pro Florida Women | 2023/06/02 16:30 | Elizabeth Fauchet v Brooklyn Olson | 0-6,1-6 |
| UTR Pro Florida Women | 2023/06/01 15:00 | Taly Licht v Brooklyn Olson | 6-4,6-2 |
| UTR Pro Winston-Salem Women | 2023/09/06 19:45 | Sophie Llewellyn v Lucia Quiterio | 1-6,6-3,3-6 |
| UTR Pro Winston-Salem Women | 2023/09/05 17:00 | Sophie Llewellyn v Rhea Verma | 6-7,6-4,6-4 |
| UTR Pro Winston-Salem Women | 2023/09/04 20:00 | Sophie Llewellyn v Whitley Pate | 3-6,6-7 |
| UTR Pro Winston-Salem Women | 2023/09/03 23:01 | Sophie Llewellyn v Anna Ulyashchenko | 5-7,7-5,6-7 |
| UTR Pro Florida Women | 2023/06/02 21:08 | Marianne Argyrokastriti v Sophie Llewellyn | 6-4,6-4 |
| UTR Pro Florida Women | 2023/06/01 20:30 | Elizabeth Ionescu v Sophie Llewellyn | 6-2,7-5 |
| UTR Pro California Women | 2023/05/07 17:00 | Mayra Jovic v Sophie Llewellyn | 5-7,6-3,3-0 |
| UTR Pro California Women | 2023/05/06 18:30 | Julia Ronney v Sophie Llewellyn | 1-6,6-3,6-7 |