Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| 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 |
| UTR Pro Tennis Series Canberra | 2021/04/21 00:00 | Casey Hoole v Dayne Kelly | 2-6,5-7 |
| ITF M25 Pensacola | 2021/05/19 16:50 | Nick Chappell v Oscar Mesquida Berg | 5-7,6-4,3-6 |
| Challenger Salinas 2 | 2021/04/28 16:35 | Nick Chappell v Tak Khunn Wang | 6-3,1-6,5-7 |
| Challenger Salinas | 2021/04/20 15:50 | Nick Chappell v Roberto Ortega-Olmedo | 3-6,2-6 |
| Challenger Oeiras Qual | 2021/04/04 15:10 | Nick Chappell v Henrique Rocha | 4-6,2-6 |
| Challenger Marbella | 2021/03/29 09:00 | Javier Barranco Cosano v Nick Chappell | 6-2,7-6 |
| Challenger Marbella | 2021/03/28 12:15 | Fermin Tenti v Nick Chappell | 0-6,0-6 |
| Challenger Lugano | 2021/03/21 09:00 | Vitaliy Sachko v Nick Chappell | 6-3,6-1 |
| Challenger Cleveland | 2021/03/16 19:10 | Nick Chappell v Roy Smith | 4-6,7-5,4-6 |