| UTR Pro Florida Women | 2023/12/19 15:00 | Brooklyn Olson v Madeline Atway | 3-6,6-4,4-6 |
| UTR Pro Florida Women | 2023/12/18 15:00 | Brooklyn Olson v Sofia E C Dominguez | 1-6,4-6 |
| UTR Pro Winston-Salem Women | 2023/09/09 23:00 | Brooklyn Olson v Sophie Llewellyn | 6-4,3-6,6-1 |
| 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 | 2023/12/17 18:36 | Tara Malik v Sena Yoon | 6-3,6-3 |