Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| Challenger Little Rock | 2021/05/31 21:00 | Goncalo Oliveira v Ryan Harrison | 7-5,7-6 |
| Challenger Tallahassee | 2021/04/21 19:00 | Ryan Harrison v Michael Mmoh | 4-6,3-6 |
| Challenger Tallahassee | 2021/04/20 14:00 | Ryan Harrison v Donald Young | 2-6,6-3,6-3 |
| ATP Delray Beach | 2021/01/07 19:30 | Gianluca Mager v Ryan Harrison | 3-6,6-1,6-4 |
| ATP Acapulco | 2020/02/23 01:00 | Daniel Altmaier v Ryan Harrison | 6-2,6-3 |
| ATP Delray Beach | 2020/02/19 17:30 | Soonwoo Kwon v Ryan Harrison | 6-4,3-6,7-6 |
| ATP Delray Beach | 2020/02/17 17:45 | Ryan Harrison v Damir Dzumhur | 6-3,6-2 |
| Challenger Cleveland | 2020/02/13 19:55 | Geoffrey Blancaneaux v Ryan Harrison | 6-3,3-6,6-2 |
| Challenger Little Rock | 2021/06/02 16:30 | Dayne Kelly v Nick Chappell | 6-1,7-5 |
| 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 |