Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| Tulsa, Singles Main, M-ITF-USA-16A | 2021/06/17 00:35 | Oliver Crawford v Shane, Ryan | 7-5,7-6 |
| Orlando, USA | 2021/06/08 17:00 | Oliver Crawford v Emilio Gomez | 6-7,7-6,3-6 |
| Challenger - Little Rock | 2021/06/03 17:00 | Kelly, Dayne v Oliver Crawford | 4-6,1-6 |
| Challenger - Little Rock | 2021/06/02 16:30 | Oliver Crawford v Polansky, Peter | 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 Cairo | 2021/05/08 11:05 | Ivanov, Simon Anthony v Oliver Crawford | 7-5,6-4 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2021/06/16 23:30 | Pervolarakis, Michail v Stefan Kozlov | 7-6,6-4 |
| ITF M25 Wichita | 2021/06/11 14:55 | Pervolarakis, Michail v Sho Shimabukuro | 3-6,3-6 |
| ITF M25 Wichita | 2021/06/10 15:40 | Pervolarakis, Michail v Dane Sweeny | 6-4,6-4 |
| ITF M25 Wichita | 2021/06/09 23:05 | Pervolarakis, Michail v Tristan Schoolkate | 7-5,6-2 |
| Challenger - Little Rock | 2021/05/30 15:00 | Pervolarakis, Michail v Sebastian Fanselow | 4-6,5-7 |
| ITF - M15 Monastir | 2021/05/20 08:20 | Thomas Fancutt v Pervolarakis, Michail | 6-4,7-5 |
| ITF - M15 Monastir | 2021/05/19 08:25 | Yuta Kikuchi v Pervolarakis, Michail | 4-6,6-7 |
| ITF - M15 Monastir | 2021/05/13 08:30 | Alexander Donski v Pervolarakis, Michail | 7-6,7-6 |