Stadium: Court 2 Round: 14 Ground: Hardcourt outdoor
| 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 Cleveland | 2020/02/13 00:05 | Ryan Harrison v Sebastian Ofner | 6-3,6-7,6-3 |
| Challenger Cleveland | 2020/02/10 23:00 | Ryan Harrison v Collin Altamirano | 6-4,7-6 |
| Challenger Dallas | 2020/02/04 03:00 | Ryan Harrison v Brandon Nakashima | 3-6,4-6 |
| UTR Pro Tennis Series Florida | 2020/12/16 16:00 | Nick Chappell v JanMagnus Johnson | 2-6,7-6,3-6 |
| UTR Pro Tennis Series Florida | 2020/12/15 17:00 | Nico Mostardi v Nick Chappell | 7-6,0-6,5-7 |
| UTR Pro Tennis Series Florida | 2020/12/14 22:00 | Nick Chappell v Evan Bynoe | 6-1,6-1 |
| ITF M15 Santo Domingo | 2020/12/12 14:55 | Nick Chappell v Nick Hardt | 3-6,2-6 |
| ITF M15 Santo Domingo | 2020/12/11 13:30 | Nick Chappell v Ezekiel Clark | 6-3,2-6,6-1 |
| ITF M15 Santo Domingo | 2020/12/10 13:30 | Nick Chappell v Reese Stalder | 6-4,7-6 |
| ITF M15 Santo Domingo | 2020/12/09 13:30 | Nick Chappell v David Volfson | 6-1,6-1 |
| ITF M15 Santo Domingo | 2020/12/05 14:30 | Nick Chappell v Oliver Crawford | 5-7,6-0,4-6 |