Jessie Aney 6-2,6-0 Brooklyn Olson 2023-09-07 18:30
Ground: Hardcourt indoor
Home History
| UTR Pro Winston-Salem Women | 2023/09/06 18:30 | Jessie Aney v Emma Wilkins | 6-1,6-0 |
| UTR Pro Winston-Salem Women | 2023/09/05 22:00 | Sankavi Gownder v Jessie Aney | 3-6,4-6 |
| UTR Pro Winston-Salem Women | 2023/09/04 22:52 | Marcella Cruz v Jessie Aney | 6-7,0-6 |
| WTA Cleveland | 2023/08/19 16:00 | Jessie Aney v Fernanda Contreras Gomez | 2-6,3-6 |
| WTA Prague | 2023/07/29 16:20 | Jessie Aney v Chloe Paquet | 6-7,2-6 |
| WTA Budapest | 2023/07/15 10:45 | Kaja Juvan v Jessie Aney | 6-2,6-0 |
| ITF W60 Amstelveen | 2023/07/12 09:00 | Jessie Aney v Isis L Van Den Broek | 5-7,6-2,2-6 |
| ITF W60 Liepaja | 2023/07/09 07:55 | Jessie Aney v Darja Semenistaja | 4-6,4-6 |
Away History
| 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 Florida Women | 2023/05/30 18:00 | Megan Heuser v Brooklyn Olson | 1-6,5-7 |
| UTR Pro Florida Women | 2023/05/29 15:00 | Brooklyn Olson v Gabriella Broadfoot | 6-7,6-1,2-6 |