Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| 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 Cairo | 2021/05/08 11:05 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 |
| ITF M15 Cairo | 2021/05/07 10:15 | Gabriel Donev v Oliver Crawford | 6-3,2-6,2-6 |
| ITF M15 Cairo | 2021/05/06 09:35 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 |
| ITF M15 Cairo | 2021/05/05 12:45 | Alex Barrena v Oliver Crawford | 0-6,2-6 |
| ITF M15 Cairo | 2021/04/30 09:10 | Oliver Crawford v Bastian Malla | 1-6,0-6 |
| French Open | 2021/05/24 10:00 | Peter Polansky v Nikola Milojevic | 6-7,6-1,2-6 |
| ATP Lyon | 2021/05/16 09:40 | Peter Polansky v Alessandro Giannessi | 3-6,4-6 |
| Challenger Prague | 2021/05/02 15:15 | Denis Istomin v Peter Polansky | 6-3,7-5 |
| Challenger Ostrava | 2021/04/27 10:00 | Peter Polansky v Lukas Klein | 3-6,5-7 |
| Challenger Tallahassee | 2021/04/19 19:10 | Peter Polansky v Michael Mmoh | 5-7,6-7 |
| Challenger Orlando | 2021/04/13 15:20 | Peter Polansky v Yasutaka Uchiyama | 3-6,6-3,4-6 |
| Challenger Nur-Sultan | 2021/03/04 05:00 | Soonwoo Kwon v Peter Polansky | 7-6,6-4 |
| Challenger Nur-Sultan | 2021/02/23 10:10 | Peter Polansky v Maximilian Marterer | 3-6,4-6 |