| 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 | 2023/06/03 14:30 | Elizabeth Ionescu v Brooklyn Olson | 6-2,4-6,6-0 |
| UTR Pro Florida Women | 2023/12/18 15:00 | Ellie Schoppe v Madeline Atway | 6-1,6-0 |
| ITF W15 Champaign | 2023/11/07 22:50 | Madeline Atway v Mary Lewis | 1-6,6-1,4-6 |
| ITF W15 Champaign | 2023/11/06 17:00 | Susanna Maltby v Madeline Atway | 4-6,1-6 |
| UTR Pro Columbus Women | 2023/08/20 14:30 | Madeline Atway v Amiya Bowles | 6-2,6-5 |
| UTR Pro Columbus Women | 2023/08/19 18:41 | Madeline Atway v Bouzgarrou, Mouna | 6-2,6-4 |
| UTR Pro Columbus Women | 2023/08/18 17:00 | Madeline Atway v Cassie Alcala | 2-6,1-6 |
| UTR Pro Columbus Women | 2023/08/16 14:00 | Madeline Atway v Alessia Cau | 2-6,2-6 |
| UTR Pro Columbus Women | 2023/08/15 18:15 | Madeline Atway v Carla Pacot | 2-6,3-6 |