Stadion: Court 22 Round: 27 Ground: Clay
| ITF - M25 - Pensacola | 2021/05/20 14:25 | Adrian Andreev v Dayne Kelly | 6-2,6-2 |
| ITF - M25 - Pensacola | 2021/05/19 16:30 | Adrian Andreev v Nicolas Barrientos | 6-4,6-2 |
| ITF - M15 - Antalya | 2021/05/09 08:50 | Alexander Erler v Adrian Andreev | 6-4,6-1 |
| ITF - M15 - Antalya | 2021/05/08 07:30 | Sandro Ehrat v Adrian Andreev | 1-6,7-5,3-6 |
| ITF - M15 - Antalya | 2021/05/07 08:35 | Sandro Kopp v Adrian Andreev | 3-6,4-6 |
| ITF - M15 - Antalya | 2021/05/06 11:40 | Gabriele Piraino v Adrian Andreev | 3-6,2-6 |
| ITF - M15 - Antalya | 2021/05/05 11:40 | Louroi Martinez v Adrian Andreev | 5-7,6-7 |
| Challenger - Oeiras | 2021/04/08 10:00 | Pedro Cachin v Adrian Andreev | 6-2,6-4 |
| 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 - Kairo | 2021/05/08 11:05 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 |
| ITF - M15 - Kairo | 2021/05/07 10:15 | Gabriel Donev v Oliver Crawford | 6-3,2-6,2-6 |
| ITF - M15 - Kairo | 2021/05/06 09:35 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 |
| ITF - M15 - Kairo | 2021/05/05 12:45 | Alex Barrena v Oliver Crawford | 0-6,2-6 |
| ITF - M15 - Kairo | 2021/04/30 09:10 | Oliver Crawford v Bastian Malla | 1-6,0-6 |
| ITF - M15 - Kairo | 2021/04/29 08:00 | Oliver Crawford v Juan Ignacio Galarza | 6-1,6-4 |