Stadium: Center Court Round: 25 Ground: Clay
| Challenger Little Rock | 2021/06/05 16:00 | Emilio Gomez v Goncalo Oliveira | 6-4,6-2 |
| Challenger Little Rock | 2021/06/03 17:50 | Mukund Sasikumar v Goncalo Oliveira | 6-4,4-6,2-6 |
| Challenger Little Rock | 2021/05/31 21:00 | Goncalo Oliveira v Ryan Harrison | 7-5,7-6 |
| Challenger Oeiras | 2021/05/26 14:45 | Goncalo Oliveira v Timofey Skatov | 3-6,1-6 |
| Challenger Oeiras | 2021/05/25 13:00 | Pedro Cachin v Goncalo Oliveira | 4-6,7-5,6-7 |
| Challenger Oeiras | 2021/05/17 09:30 | Emilio Gomez v Goncalo Oliveira | 6-2,3-6,6-4 |
| Challenger Oeiras | 2021/05/16 12:30 | Goncalo Oliveira v Maxime Janvier | 6-3,6-4 |
| Challenger Oeiras | 2021/04/09 14:55 | Goncalo Oliveira v Tiago Cacao | 7-5,6-2 |
| Challenger Lyon | 2021/06/06 09:30 | Michael Vrbensky v Evan King | 4-6,2-6 |
| ITF - Most M25 | 2021/05/26 08:00 | Michael Vrbensky v Lucas Bouquet | 7-5,3-6,4-6 |
| ITF - Jablonec Nad Nisou M25 | 2021/05/19 10:00 | Jack Draper v Michael Vrbensky | 4-6,7-6,6-2 |
| Challenger Praga | 2021/05/08 09:00 | Michael Vrbensky v Oscar Otte | 3-6,3-6 |
| Challenger Praga | 2021/05/07 09:00 | Vit Kopriva v Michael Vrbensky | 1-6,4-6 |
| Challenger Praga | 2021/05/05 09:00 | Michael Vrbensky v Andrej Martin | 6-4,1-6,6-4 |
| Challenger Praga | 2021/05/03 14:05 | Michael Vrbensky v Sebastian Ofner | 7-6,6-3 |
| Challenger Ostrava | 2021/04/25 10:00 | Michael Vrbensky v Alex Molcan | 3-6,4-6 |