Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| Challenger Little Rock | 2021/06/02 16:30 | Dayne Kelly v Nick Chappell | 6-1,7-5 |
| Challenger Little Rock | 2021/05/31 15:00 | Gage Brymer v Dayne Kelly | 2-6,1-6 |
| Challenger Little Rock | 2021/05/30 16:15 | Patrick Kypson v Dayne Kelly | 6-4,3-6,2-6 |
| ITF M25 Pensacola | 2021/05/20 14:25 | Adrian Andreev v Dayne Kelly | 6-2,6-2 |
| ITF M25 Pensacola | 2021/05/19 17:00 | Alejandro Gomez v Dayne Kelly | 4-6,4-6 |
| UTR Pro Tennis Series Canberra | 2021/04/24 01:30 | Dane Sweeny v Dayne Kelly | 6-2,6-4 |
| UTR Pro Tennis Series Canberra | 2021/04/23 01:30 | Dayne Kelly v Omar Jasika | 6-0,5-3 |
| UTR Pro Tennis Series Canberra | 2021/04/22 03:00 | Dayne Kelly v Scott Puodziunas | 6-2,6-2 |
| 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 M15 Cairo | 2021/05/06 09:35 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 |
| ITF M15 Cairo | 2021/05/05 12:45 | Alex Barrena v Oliver Crawford | 0-6,2-6 |