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