Stadium: Cancha 5 Round: 26 Ground: Clay
| Challenger Bogota | 2021/10/19 15:00 | Alejandro Gomez v Jaroslav Pospisil | 6-3,3-6,7-5 |
| Challenger Bogota | 2021/10/18 15:00 | Bart Stevens v Jaroslav Pospisil | 6-3,6-7,3-6 |
| Challenger Bogota | 2021/10/17 15:00 | Jaroslav Pospisil v Jean Thirouin | 6-4,6-7,6-2 |
| ITF M25 Budapest | 2021/09/29 11:10 | Gergely Madarasz v Jaroslav Pospisil | 6-4,1-6,7-5 |
| ITF M25 Prostejov | 2021/08/16 10:50 | Jaroslav Pospisil v Nicolas Alvarez Varona | 3-6,3-6 |
| Challenger Meerbusch | 2021/08/08 10:00 | Duje Ajdukovic v Jaroslav Pospisil | 6-3,6-2 |
| Challenger Liberec | 2021/08/01 15:00 | Alexander Ritschard v Jaroslav Pospisil | 6-2,6-4 |
| ITF M15 Poprad | 2021/07/08 07:55 | Milos Karol v Jaroslav Pospisil | 6-4,7-6 |
| Challenger Santiago | 2021/10/12 14:00 | Dalibor Svrcina v Diego Hidalgo | 6-2,6-0 |
| Challenger Santiago | 2021/10/11 14:00 | Diego Hidalgo v Mathieu Perchicot | 2-6,6-3,6-4 |
| Challenger Santiago Qual | 2021/10/10 14:20 | Shintaro Mochizuki v Diego Hidalgo | 0-6,3-6 |
| Challenger Santiago | 2021/10/03 17:25 | Facundo Diaz Acosta v Diego Hidalgo | 6-3,7-6 |
| Challenger Ambato | 2021/09/22 15:00 | Diego Hidalgo v Facundo Mena | 4-6,3-6 |
| Challenger Quito | 2021/09/13 20:00 | Roberto Quiroz v Diego Hidalgo | 6-4,7-5 |
| Challenger Pozoblanco | 2021/07/19 15:00 | Michael Geerts v Diego Hidalgo | 7-6,6-3 |
| Challenger Pozoblanco | 2021/07/18 17:45 | Carlos Matarredona Valor v Diego Hidalgo | 4-6,5-7 |