Stadium: Pista 2 Round: 25 Ground: Clay
| Challenger Warsaw | 2021/08/25 08:00 | Szymon Kielan v Goncalo Oliveira | 7-5,6-0 |
| Challenger Verona | 2021/08/17 12:10 | Goncalo Oliveira v Paolo Lorenzi | 3-6,3-6 |
| Challenger Prague | 2021/08/11 09:50 | Goncalo Oliveira v Dmitry Popko | 0-6,3-6 |
| Challenger Prague | 2021/08/10 09:30 | Toby Alex Kodat v Goncalo Oliveira | 3-6,1-6 |
| Challenger Segovia | 2021/07/27 09:30 | Alejandro Moro Canas v Goncalo Oliveira | 3-6,7-6,6-1 |
| Challenger Amersfoort | 2021/07/13 10:00 | Goncalo Oliveira v Botic Van De Zandschulp | 2-6,4-6 |
| Challenger Porto | 2021/07/02 12:00 | Goncalo Oliveira v Sergiy Stakhovsky | 6-7,6-7 |
| Challenger Porto | 2021/06/30 10:00 | Peter Polansky v Goncalo Oliveira | 6-7,4-6 |
| Challenger Como | 2021/08/31 15:15 | Julian Lenz v Jozef Kovalik | 5-7,2-6 |
| Challenger Warsaw | 2021/08/24 14:45 | Lukas Klein v Julian Lenz | 6-1,3-6,6-3 |
| Challenger Luedenscheid | 2021/08/21 12:35 | Julian Lenz v Nicolas Jarry | 1-6,4-6 |
| Challenger Luedenscheid | 2021/08/20 11:30 | Mirza Basic v Julian Lenz | 5-7,5-7 |
| Challenger Luedenscheid | 2021/08/18 12:45 | Julian Lenz v Roman Safiullin | 5-7,6-4,6-2 |
| Challenger Luedenscheid | 2021/08/17 08:00 | Julian Lenz v Shintaro Mochizuki | 5-7,7-5,6-2 |
| ITF M25 Wetzlar | 2021/08/04 14:30 | Julian Lenz v David Pichler | 1-6,5-7 |
| Challenger Trieste | 2021/07/28 10:00 | Julian Lenz v Orlando Luz | 5-7,0-6 |