| UTR Pro Tennis Series Florida | 2021/01/15 17:00 | Matt Kuhar v Omar Maldonado | 6-0,6-3 |
| UTR Pro Tennis Series Florida | 2021/01/13 14:00 | Nico Mostardi v Omar Maldonado | 4-6,4-6 |
| UTR Pro Tennis Series Florida | 2021/01/12 20:00 | Noah Rubin v Omar Maldonado | 6-1,5-2 |
| UTR Pro Tennis Series Florida | 2021/01/11 14:00 | John Bernard v Omar Maldonado | 6-0,5-4 |
| UTR Pro Tennis Series Florida | 2021/08/22 12:00 | Antonio M-Hidalgo v Theo Winegar | 6-7,6-1,6-1 |
| UTR Pro Tennis Series Florida | 2021/08/21 13:30 | Huzaifa Abdul Rehman v Theo Winegar | 2-6,1-5 |
| UTR Pro Tennis Series Florida | 2021/08/19 15:17 | Theo Winegar v Matthew Segura | 4-6,6-3,6-3 |
| UTR Pro Tennis Series Florida | 2021/08/18 16:00 | Theo Winegar v Chase Ferguson | 4-6,5-7 |
| UTR Pro Tennis Series Florida | 2021/08/17 14:30 | Theo Winegar v William Mroz Mroz | 2-6,6-3,6-0 |
| UTR Pro Tennis Series Florida | 2021/08/16 17:30 | Theo Winegar v Michael Nicholls | 7-5,5-2 |