| UTR Pro Tennis Series Florida Women | 2021/09/11 15:30 | Sydney Berlin v Brooklyn Olson | 6-3,5-2 |
| UTR Pro Tennis Series Florida Women | 2021/09/09 12:00 | Brooklyn Olson v Emma Shelton | 3-6,0-6 |
| UTR Pro Tennis Series Florida Women | 2021/09/08 15:00 | Sophie Chang v Brooklyn Olson | 6-3,6-4 |
| UTR Pro Tennis Series Florida Women | 2021/09/07 16:30 | Blanka Demicheli v Brooklyn Olson | 7-6,3-6,1-6 |
| ITF W25 Pelham | 2021/05/19 15:00 | Brooklyn Olson v Marcela Zacarias | 1-6,0-6 |
| ITF W25 Pelham | 2021/05/18 16:55 | Brooklyn Olson v Kelly Williford | 6-1,6-4 |
| 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 | 2021/09/09 15:00 | Sophie Chang v Victoria Osuigwe | 6-1,6-0 |
| UTR Pro Tennis Series Florida Women | 2021/06/12 16:00 | Emma Fernald v Victoria Osuigwe | 6-0,6-2 |
| UTR Pro Tennis Series Florida Women | 2021/06/11 17:30 | Ava Markham v Victoria Osuigwe | 3-6,6-0,5-4 |
| UTR Pro Tennis Series Florida Women | 2021/06/10 16:00 | Jingyi Li v Victoria Osuigwe | 6-3,7-5 |