Estádio: Court 5 Round: 25 Ground: Hardcourt outdoor
| 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 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 - M25 Tulsa | 2021/06/15 15:55 | Ryan Shane v Joshua Ortlip | 5-7,6-4,10-5 |
| ITF - M25 Tulsa | 2021/06/14 18:00 | Ryan Shane v Bradley Frye | 6-3,6-2 |
| ITF - M25 Wichita | 2021/06/09 18:15 | Ryan Shane v Nicolas Acevedo | 5-7,6-4,2-6 |
| UTR Pro Tennis Series - Atlanta | 2021/04/10 12:30 | Roberto Cid Subervi v Ryan Shane | 6-3,3-6,5-3 |
| UTR Pro Tennis Series - Atlanta | 2021/04/08 12:30 | Ryan Shane v McClain Kessler | 6-2,5-3 |
| UTR Pro Tennis Series - Atlanta | 2021/04/07 18:00 | Ryan Shane v Adit Sinha | 6-4,5-7,6-3 |
| UTR Pro Tennis Series - Atlanta | 2021/04/06 17:00 | Ryan Shane v Valentino Raul Caratini | 4-6,6-0,6-1 |
| UTR Pro Tennis Series - Atlanta | 2021/04/05 15:30 | Ryan Shane v Aditya Vashistha | 5-7,0-5 |