| UTR Pro Tennis Series Florida | 2021/08/28 15:00 | Theo Winegar v Parth Aggarwal | 5-1 |
| UTR Pro Tennis Series Florida | 2021/08/27 13:30 | Theo Winegar v Juan David Velasquez | 3-6,6-4,6-1 |
| 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 | 2021/08/28 15:00 | Duilio Vallebuona v Daniel Mora | 6-3,1-1 |
| UTR Pro Tennis Series Florida | 2021/08/26 16:30 | Duilio Vallebuona v Jake Van Emburgh | 4-6,6-4,3-5 |
| UTR Pro Tennis Series Florida | 2021/08/25 15:00 | Brian Berdusco v Duilio Vallebuona | 6-3,6-4 |
| UTR Pro Tennis Series Florida | 2021/08/24 12:00 | Toby D. Boyer v Duilio Vallebuona | 6-2,7-6 |
| UTR Pro Tennis Series Florida | 2021/08/20 16:00 | Duilio Vallebuona v Jorge Panta | 4-6,1-6 |
| 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 | 2021/08/18 16:00 | Rithvik Choudary Bollipalli v Duilio Vallebuona | 6-4,3-6,5-3 |
| UTR Pro Tennis Series Florida | 2021/08/17 14:30 | Antonio M-Hidalgo v Duilio Vallebuona | 6-3,6-2 |