| 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 | 2023/06/03 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 |
| Billie Jean King Cup | 2023/07/29 13:25 | Taly Licht v Sofia E C Dominguez | 2-6,3-6 |
| Billie Jean King Cup | 2023/07/28 15:00 | Lara Escauriza v Sofia E C Dominguez | 1-6,4-6 |
| Billie Jean King Cup | 2023/07/27 18:30 | Sofia E C Dominguez v Elana Mackey | 6-0,6-1 |
| Billie Jean King Cup | 2023/07/26 13:30 | Sofia E C Dominguez v Lucia Gallegos | 6-2,6-1 |