| 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 | 2021/08/21 15:00 | Henry Lieberman v Mateo Barreiros Reyes | 5-7,2-6 |
| UTR Pro Tennis Series Florida | 2021/08/20 12:00 | Henry Lieberman v Matthis Ross | 3-6,3-6 |
| UTR Pro Tennis Series Florida | 2021/08/19 18:30 | Henry Lieberman v Huzaifa Abdul Rehman | 6-1,6-2 |
| UTR Pro Tennis Series Florida | 2021/08/18 13:00 | Henry Lieberman v Rafael Lima Wagner | 2-6,6-3,6-1 |
| UTR Pro Tennis Series Florida | 2021/08/16 12:51 | Lukas Greif v Henry Lieberman | 2-6,7-5,5-1 |
| UTR Pro Pro Tennis Tennis Series Atlanta | 2021/07/11 18:30 | Valentino Raul Caratini v Henry Lieberman | 2-6,1-5 |
| UTR Pro Pro Tennis Tennis Series Atlanta | 2021/07/10 13:30 | Henry Lieberman v Jacob Bickersteth | 6-7,2-5 |
| UTR Pro Pro Tennis Tennis Series Atlanta | 2021/07/08 13:30 | Juan Pablo Cenoz v Henry Lieberman | 2-6,6-7 |