Stadium: Court 1 Round: 14 Ground: Clay
| Challenger - Cordenons | 2021/08/01 09:00 | Camilo Ugo Carabelli v Rafael Matos | 4-6,7-5,6-2 |
| Challenger - Aix en Provence | 2021/06/13 11:15 | Nikolas Sanchez Izquierdo v Rafael Matos | 6-2,6-2 |
| Challenger - Tallahassee | 2021/04/18 19:30 | Rafael Matos v Sekou Bangoura | 3-6,4-6 |
| Challenger - Santiago | 2021/03/16 17:10 | Pedro Sousa v Rafael Matos | 6-4,6-3 |
| Challenger - Santiago | 2021/03/15 13:00 | Joao Menezes v Rafael Matos | 6-2,6-4 |
| Challenger - Santiago | 2021/03/14 14:00 | Luis David Martinez v Rafael Matos | 2-6,3-6 |
| ATP - Santiago | 2021/03/06 13:00 | Rafael Matos v Pedro Sakamoto | 3-6,1-6 |
| Challenger - Concepcion | 2021/02/15 15:40 | Thiago Agustin Tirante v Rafael Matos | 6-3,2-6,6-3 |
| ITF M25 - Caslano | 2021/08/26 14:30 | Giovanni Oradini v Tobias Simon | 4-6,6-4,3-6 |
| ITF M25 - Caslano | 2021/08/25 13:10 | Stefano Baldoni v Tobias Simon | 6-7,1-6 |
| ITF M25 - Frankfurt am Main | 2021/08/10 13:55 | Tobias Simon v Christian Sigsgaard | 3-6,3-6 |
| ITF M25 - Bakio | 2021/06/29 13:00 | Pablo Llamas Ruiz v Tobias Simon | 7-5,6-2 |
| ITF M25 - Klosters | 2021/06/24 08:35 | Dominic Stephan Stricker v Tobias Simon | 7-6,6-7,6-3 |
| ITF M25 - Klosters | 2021/06/23 12:00 | Tomas Papik v Tobias Simon | 3-6,4-6 |
| Challenger - Forlì | 2021/06/14 09:30 | Thiago Agustin Tirante v Tobias Simon | 7-6,6-3 |
| Challenger - Forlì | 2021/06/13 14:15 | Matteo Arnaldi v Tobias Simon | 6-7,2-6 |