| UTR Pro Tennis Series Miami | 2021/11/06 15:30 | Matthew Segura v Maximiliano Estevez | 2-6,3-6 |
| UTR Pro Tennis Series Miami | 2021/11/04 17:00 | Matthew Segura v Juan David Velasquez | 6-4,5-4 |
| UTR Pro Tennis Series Miami | 2021/11/03 17:00 | Jerry Barton v Matthew Segura | 4-6,3-5 |
| UTR Pro Tennis Series Miami | 2021/11/02 18:30 | Bruno Vietri v Matthew Segura | 7-5,2-6,4-6 |
| ITF M15 Vero Beach | 2021/10/22 19:00 | Matthew Segura v Ezekiel Clark | 5-7,4-6 |
| ITF M15 Vero Beach | 2021/10/20 22:00 | Matthew Segura v Cooper Williams | 1-6,6-3,6-1 |
| UTR Pro Tennis Series Florida | 2021/09/19 14:00 | Matthew Segura v Roman Postolka | 1-1 |
| UTR Pro Tennis Series Florida | 2021/09/18 17:30 | Matthew Segura v Brian Berdusco | 6-3,5-2 |
| UTR Pro Tennis Series Miami | 2021/11/04 20:00 | Henry Lieberman v Geronimo E Busleiman | 6-3,6-1 |
| UTR Pro Tennis Series Miami | 2021/11/03 20:00 | Henry Lieberman v Jake Fellows | 7-6,5-3 |
| UTR Pro Tennis Series Miami | 2021/11/02 17:00 | Henry Lieberman v Francisco Bastias | 6-4,3-6,3-6 |
| UTR Pro Tennis Series Miami | 2021/11/01 16:30 | Henry Lieberman v Timothy Phung | 7-5,5-4 |
| UTR Pro Tennis Series Florida | 2021/08/28 12:00 | Henry Lieberman v Jorge Panta | 6-3,3-6,1-5 |
| UTR Pro Tennis Series Florida | 2021/08/27 12:00 | Henry Lieberman v Top Nidunjianzan | 6-3,7-6 |
| 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 | 2021/08/25 13:00 | Omar Maldonado v Henry Lieberman | 6-3,4-6,4-6 |