Stadium: Stadium Round: 27 Ground: Hardcourt outdoor
| 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 - Oeiras | 2021/04/08 15:50 | Oscar Otte v Goncalo Oliveira | 4-6,6-4,3-6 |
| Challenger - Little Rock | 2021/06/03 17:00 | Dayne Kelly v Oliver Crawford | 4-6,1-6 |
| Challenger - Little Rock | 2021/06/02 16:30 | Oliver Crawford v Peter Polansky | 7-5,6-2 |
| ITF - M25 Pensacola | 2021/05/21 14:25 | Adrian Andreev v Oliver Crawford | 6-2,6-3 |
| ITF - M25 Pensacola | 2021/05/20 16:25 | Oliver Crawford v Christian Harrison | 6-4,7-6 |
| ITF - M25 Pensacola | 2021/05/19 14:30 | Mwendwa Mbithi v Oliver Crawford | 5-7,4-6 |
| ITF M15 - Caïro | 2021/05/08 11:05 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 |
| ITF M15 - Caïro | 2021/05/07 10:15 | Gabriel Donev v Oliver Crawford | 6-3,2-6,2-6 |
| ITF M15 - Caïro | 2021/05/06 09:35 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 |