Stadium: Court 4 Round: 26 Ground: Hardcourt outdoor
| 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 - Sharm El Sheikh | 2020/10/28 08:00 | Dusty H. Boyer v Nick Chappell | 4-6,7-6,1-6 |
| ITF M15 - Sharm El Sheikh | 2020/10/22 07:00 | Nick Chappell v Vladyslav Manafov | 3-6,2-6 |
| ITF M15 - Santo Domingo | 2020/12/02 13:30 | Connor Farren v Jesse Flores | 4-6,6-7 |
| ITF M15 - Santo Domingo | 2020/12/01 13:30 | Dominik Palan v Jesse Flores | 3-6,1-6 |
| ITF M15 - Santo Domingo | 2020/11/30 15:00 | Jack Vance v Jesse Flores | 1-6,2-6 |
| ITF M15 - Santo Domingo | 2020/11/29 14:30 | Tennyson Whiting v Jesse Flores | 3-6,2-6 |
| ITF M15 - Sharm El Sheikh | 2020/11/11 13:05 | Jesse Flores v Kelsey Stevenson | 3-6,5-7 |
| ITF M15 - Sharm El Sheikh | 2020/11/02 10:30 | Arjun Kadhe v Jesse Flores | 6-3,6-2 |
| ITF M15 - Sharm El Sheikh | 2020/11/01 12:00 | Jesse Flores v Seth Seely | 6-3,6-1 |
| ITF M15 - Sharm El Sheikh | 2020/10/26 08:00 | Daniele Capecchi v Jesse Flores | 6-3,3-6,10-3 |