| UTR Pro Tennis Series Florida | 2021/01/10 16:00 | Nick Chappell v Matthew Segura | 0-0 |
| 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 |
| UTR Pro Tennis Series Florida | 2021/01/10 16:30 | Anze Arh v Drew Van Orderlain | 6-1,3-6,0-3 |
| ITF Canada F7 | 2018/09/08 13:00 | Perry Gregg v Drew Van Orderlain | 6-3,6-4 |
| ITF Canada F6 | 2018/09/02 13:00 | Maxime Cressy v Drew Van Orderlain | 6-2,6-3 |
| ITF Canada F6 | 2018/09/01 15:00 | Sebastian Zapata v Drew Van Orderlain | 2-6,0-6 |
| ITF USA F23 Qual | 2018/08/13 15:45 | Drew Van Orderlain v Jason Seidman | 4-6,4-6 |
| ITF USA F23 Qual | 2018/08/12 14:00 | Sergio Luis H Ramirez v Drew Van Orderlain | 1-6,5-7 |
| ITF Canada F5 Qual | 2018/07/02 16:00 | Joshua Peck v Drew Van Orderlain | 6-2,6-3 |
| ITF Canada F4 Qual | 2018/06/24 17:00 | Justin Roberts v Drew Van Orderlain | 6-4,6-3 |