Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| Challenger Orlando | 2020/11/14 15:00 | Roy Smith v Nick Chappell | 6-7,1-6 |
| UTR Pro Tennis Series Florida | 2021/01/20 19:00 | Nick Chappell v Aditya Vashistha | 6-4,5-4 |
| UTR Pro Tennis Series Florida | 2021/01/19 14:00 | Nick Chappell v Daniel Milavsky | 6-2,6-5 |
| UTR Pro Tennis Series Florida | 2021/01/18 18:30 | Nick Chappell v Matt Kuhar | 6-0,5-2 |
| UTR Pro Tennis Series Florida | 2021/01/16 18:00 | Nick Chappell v Joshua Sheehy | 3-6,0-0 |
| UTR Pro Tennis Series Florida | 2021/01/14 18:11 | Nick Chappell v Connor Krug | 7-5,6-4 |
| UTR Pro Tennis Series Florida | 2021/01/13 16:30 | Nick Chappell v Anze Arh | 6-0,6-1 |
| UTR Pro Tennis Series Florida | 2021/01/11 18:30 | Nick Chappell v Drew Van Orderlain | 6-1,7-5 |
| UTR Pro Tennis Series Florida | 2020/12/16 16:00 | Nick Chappell v JanMagnus Johnson | 2-6,7-6,3-6 |
| ITF M15 Santo Domingo | 2020/12/12 14:45 | Roy Smith v Oliver Crawford | 6-2,1-6,4-6 |
| ITF M15 Santo Domingo | 2020/12/11 13:30 | Roy Smith v Shintaro Mochizuki | 6-3,6-3 |
| ITF M15 Santo Domingo | 2020/12/10 15:25 | Roy Smith v Jurgen Briand | 7-6,6-4 |
| ITF M15 Santo Domingo | 2020/12/08 16:50 | Roy Smith v Antonio Cayetano March | 6-4,6-4 |
| ITF M15 Santo Domingo | 2020/12/03 13:30 | Leonardo Civita-Telles v Roy Smith | 6-3,6-3 |
| ITF M15 Santo Domingo | 2020/12/01 14:30 | Justin Roberts v Roy Smith | 4-6,2-6 |
| Challenger Orlando | 2020/11/14 15:00 | Roy Smith v Nick Chappell | 6-7,1-6 |
| ITF M25 Rodez | 2020/10/12 14:50 | Quentin Robert v Roy Smith | 6-4,6-3 |