Stadium: Stadium 1 Round: 19 Ground: Hardcourt outdoor
| Challenger Little Rock | 2019/06/05 18:40 | Darian King v Oliver Crawford | 6-4,6-4 |
| Challenger Lexington | 2021/07/25 15:00 | Darian King v Gabriel Diallo | 6-2,3-6,6-3 |
| ATP Newport | 2021/07/11 21:40 | Darian King v Ramkumar Ramanathan | 3-6,4-6 |
| Challenger Orlando | 2021/06/07 20:15 | Jenson Brooksby v Darian King | 7-6,6-3 |
| Challenger Little Rock | 2021/06/02 21:00 | Darian King v Mitchell Krueger | 3-6,2-6 |
| Challenger Little Rock | 2021/05/31 19:35 | Darian King v Thiago Agustin Tirante | 6-4,6-4 |
| ATP Belgrade | 2021/05/22 14:25 | Christopher O'Connell v Darian King | 6-1,6-3 |
| Challenger Orlando | 2021/04/12 15:30 | Jesper De Jong v Darian King | 6-0,6-3 |
| Challenger Cleveland | 2021/03/17 15:15 | Christopher Eubanks v Darian King | 6-1,6-2 |
| Challenger Lexington | 2021/07/25 15:00 | Oliver Crawford v Aleksandar Kovacevic | 7-6,7-5 |
| Challenger Cary | 2021/07/18 15:00 | Oliver Crawford v Trent Bryde | 6-7,2-6 |
| 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 |