| UTR Pro Tennis Series Florida | 2021/08/24 13:30 | Theo Winegar v Henry Lieberman | 3-6,1-5 |
| UTR Pro Tennis Series Florida | 2021/08/23 15:00 | Omar Maldonado v Theo Winegar | 6-4,5-3 |
| 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 |
| UTR Pro Tennis Series Florida | 2021/08/26 15:30 | Henry Lieberman v Juan David Velasquez | 6-4,6-0 |
| UTR Pro Tennis Series Florida | 2021/08/24 13:30 | Omar Maldonado v Juan David Velasquez | 6-1,3-6,3-5 |
| UTR Pro Tennis Series Florida | 2021/08/21 12:00 | Chase Ferguson v Juan David Velasquez | 6-2,6-1 |
| UTR Pro Tennis Series Florida | 2021/08/20 14:00 | Antonio M-Hidalgo v Juan David Velasquez | 5-7,2-6 |
| UTR Pro Tennis Series Florida | 2021/08/19 12:00 | Duilio Vallebuona v Juan David Velasquez | 4-6,6-1,5-7 |
| UTR Pro Tennis Series Florida | 2021/08/17 13:00 | Rithvik Choudary Bollipalli v Juan David Velasquez | 1-6,6-7 |
| UTR Pro Tennis Series Florida | 2021/08/16 16:00 | Juan David Velasquez v Jorge Panta | 3-6,3-5 |
| ITF M25 Naples | 2021/02/15 16:00 | Juan David Velasquez v Quentin Folliot | 1-6,5-7 |