Stadium: Cancha 3 Round: 25 Ground: Clay
| Challenger - Lissabon | 2021/09/29 14:10 | Andrej Martin v Goncalo Oliveira | 2-6,6-4,6-3 |
| Challenger - Lissabon | 2021/09/27 13:00 | Goncalo Oliveira v Pedro Araujo | 7-6,6-4 |
| Challenger - Quito | 2021/09/14 18:20 | Eduard Esteve Lobato v Goncalo Oliveira | 6-2,6-3 |
| Challenger - Sevilla | 2021/09/06 17:00 | Goncalo Oliveira v Julian Lenz | 2-6,6-4,2-6 |
| Challenger - Warschau | 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 - Praag | 2021/08/11 09:50 | Goncalo Oliveira v Dmitry Popko | 0-6,3-6 |
| Challenger - Praag | 2021/08/10 09:30 | Toby Alex Kodat v Goncalo Oliveira | 3-6,1-6 |
| Challenger - Santiago | 2021/10/04 16:00 | Oliver Crawford v Jonathan Mridha | 7-5,6-3 |
| Challenger - Santiago | 2021/10/03 14:00 | Oliver Crawford v Daniel Antonio Nunez | 7-5,6-2 |
| ITF M25 - Sierre | 2021/09/05 08:50 | Rinky Hijikata v Oliver Crawford | 7-6,6-1 |
| ITF M25 - Sierre | 2021/09/04 10:20 | Patrick Kypson v Oliver Crawford | 3-6,4-6 |
| ITF M25 - Sierre | 2021/09/03 10:00 | Valentin Vacherot v Oliver Crawford | 3-6,6-7 |
| ITF M25 - Sierre | 2021/09/02 12:45 | Mirko Martinez v Oliver Crawford | 1-6,2-6 |
| ITF M25 - Sierre | 2021/09/01 13:40 | Louroi Martinez v Oliver Crawford | 3-6,4-6 |
| ITF M25 - Trier | 2021/08/25 15:00 | Henri Squire v Oliver Crawford | 3-6,6-1,6-2 |