| UTR Pro Tennis Series Charleston Women | 2021/10/25 17:30 | Makenna Jones v Brooklyn Olson | 6-4,6-1 |
| UTR Pro Tennis Series Florida Women | 2021/09/13 15:00 | Brooklyn Olson v Victoria Osuigwe | 0-0 |
| 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 |