Stadium: Court 13 Round: 14 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 Cairo | 2021/05/08 11:05 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 |
| ITF M25 Tulsa | 2021/06/16 23:30 | Trent Bryde v Nicolas Barrientos | 3-6,3-6 |
| ITF M25 Tulsa | 2021/06/15 16:30 | Trent Bryde v Nicaise Muamba | 6-1,6-4 |
| ITF M25 Tulsa | 2021/06/14 18:00 | Alexander Brown v Trent Bryde | 3-6,0-6 |
| ITF M25 Wichita | 2021/06/09 17:45 | Trent Bryde v Alexander Sarkissian | 3-6,6-0,4-6 |
| ITF M15 Fayetteville | 2020/11/05 15:50 | Trent Bryde v Roberto Quiroz | 3-6,7-5,3-6 |
| ITF M15 Fayetteville | 2020/11/04 17:30 | Alexandre Reco v Trent Bryde | 1-6,2-6 |
| ITF M25 Fayetteville | 2020/11/03 16:00 | Zane Khan v Trent Bryde | 5-7,5-7 |
| ITF M25 Fayetteville | 2020/11/02 19:00 | Jacob Brumm v Trent Bryde | 2-6,1-6 |