Stadium: Court 11 Round: 24 Ground: Clay
| ITF W25 Pelham | 2021/05/17 15:00 | Brooklyn Olson v Tiphanie Lemaitre | 3-6,7-5,10-4 |
| ITF W25 Pelham | 2021/05/16 15:00 | Amy Zhu v Brooklyn Olson | 5-7,3-6 |
| UTR Pro Tennis Series Florida Women | 2021/05/02 13:00 | Brooklyn Olson v Nibedita Ghosh | 6-2,2-6,4-6 |
| UTR Pro Tennis Series Florida Women | 2021/05/01 14:30 | Allura Zamarripa v Brooklyn Olson | 0-6,0-5 |
| UTR Pro Tennis Series Florida Women | 2021/04/28 18:15 | Brooklyn Olson v Irina Fetecau | 1-6,2-6 |
| UTR Pro Tennis Series Florida Women | 2021/04/27 13:00 | Brooklyn Olson v Nicole Conard | 7-6,6-3 |
| UTR Pro Tennis Series Florida Women | 2021/04/26 13:00 | Sofia Rojas v Brooklyn Olson | 7-6,4-6,5-4 |
| ITF W25 Orlando | 2020/11/11 14:50 | Emiliana Arango v Brooklyn Olson | 6-1,6-2 |
| ITF W25 Pelham | 2021/05/17 15:00 | Mckenna Schaefbauer v Kelly Williford | 6-2,6-3 |
| ITF W25 Pelham | 2021/05/16 15:00 | Kelly Williford v Jessy Rompies | 6-2,6-4 |
| ITF W15 Cancun | 2020/03/10 15:00 | Akilah James v Kelly Williford | 6-4,6-1 |
| ITF W15 Cancun | 2020/02/18 13:55 | Kelly Williford v Carolina Alves | 1-6,0-6 |
| ITF W15 Norman | 2019/12/04 18:00 | Pamela Montez v Kelly Williford | 7-5,6-2 |
| ITF W15 Cancun | 2019/11/21 16:00 | Elle Christensen v Kelly Williford | 6-0,6-4 |
| ITF W15 Cancun | 2019/11/19 15:45 | Vivian Mayumi Toma v Kelly Williford | 1-6,1-6 |
| ITF W15 Cancun | 2019/11/14 20:15 | Mayuka Aikawa v Kelly Williford | 6-2,6-2 |