Stadium: Stadium Round: 28 Ground: Hardcourt outdoor
| ITF M15 Santo Domingo | 2020/12/04 14:45 | Nick Chappell v Leonardo Civita-Telles | 6-4,7-5 |
| ITF M15 Santo Domingo | 2020/12/03 15:55 | Nick Chappell v Jesse Flores | 6-3,7-6 |
| ITF M15 Santo Domingo | 2020/12/01 16:55 | Nick Chappell v Dusty H. Boyer | 7-6,6-2 |
| Challenger Orlando | 2020/11/19 17:00 | Alexander Ritschard v Nick Chappell | 6-3,6-4 |
| Challenger Orlando | 2020/11/17 18:35 | Nick Chappell v Ramkumar Ramanathan | 6-3,6-4 |
| Challenger Orlando | 2020/11/15 15:00 | Christian Harrison v Nick Chappell | 7-6,6-3 |
| Challenger Orlando | 2020/11/14 15:00 | Roy Smith v Nick Chappell | 6-7,1-6 |
| ITF M15 Sharm El Sheikh | 2020/10/29 09:25 | Yann Marti v Nick Chappell | 5-7,6-2,6-1 |
| ITF M15 Santo Domingo | 2020/12/04 17:30 | Oliver Crawford v Zane Khan | 6-3,6-2 |
| ITF M15 Santo Domingo | 2020/12/03 13:30 | Felix Corwin v Oliver Crawford | 5-7,3-6 |
| ITF M15 Santo Domingo | 2020/12/01 14:30 | Dhruva Mulye v Oliver Crawford | 0-6,0-6 |
| UTR Pro Tennis Series Cancun | 2020/11/22 16:30 | Oliver Crawford v Gage Brymer | 6-3,6-2 |
| UTR Pro Tennis Series Cancun | 2020/11/21 15:45 | Oliver Crawford v Nicolas Barrientos | 6-3,6-3 |
| UTR Pro Tennis Series Cancun | 2020/11/20 14:00 | Oliver Crawford v Manuel Sanchez | 6-2,6-4 |
| UTR Pro Tennis Series Cancun | 2020/11/19 17:00 | Oliver Crawford v Eric Samuelsson | 6-2,5-1 |
| UTR Pro Tennis Series Cancun | 2020/11/17 18:45 | Oliver Crawford v Alejandro H Franco | 3-1 |