Stadion: Cancha 1 Round: 25 Ground: Clay
| Challenger - Santiago | 2021/10/11 15:40 | Daniel Antonio Nunez v Rafael Matos | 4-6,6-7 |
| Challenger - Santiago | 2021/10/03 14:00 | Alexis Gautier v Rafael Matos | 6-3,6-2 |
| Challenger - Tulln | 2021/09/05 13:00 | Rafael Matos v Tobias Simon | 6-7,2-6 |
| 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 | 2021/10/04 22:55 | Diego F Flores v Nick Chappell | 3-6,6-3,5-7 |
| ITF - M15 - Melilla | 2021/09/25 07:00 | Oscar Mesquida Berg v Diego F Flores | 6-3,7-5 |
| ITF - M15 - Melilla | 2021/09/24 10:00 | Aaron Cohen v Diego F Flores | 3-6,6-4,3-6 |
| ITF - M25 - Sintra | 2021/09/15 11:55 | Yuta Shimizu v Diego F Flores | 6-2,6-7,6-2 |
| ITF - M25 - Sintra | 2021/09/14 13:15 | Diego F Flores v Hans Albert Schubert | 6-2,6-3 |
| ITF - M25 - Sintra | 2021/09/13 15:05 | Diego F Flores v Jaime Faria | 6-3,6-2 |
| ITF - M25 - Sintra | 2021/09/07 08:30 | Diego F Flores v Daniel Little | 6-4,0-6,6-10 |
| ITF - M25 - Sintra | 2021/09/06 10:05 | Diego F Flores v Alan Gleeson | 6-3,6-3 |