Stadium: Cancha 1 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Santo Domingo | 2020/12/03 15:55 | Nick Chappell v Jesse Flores | 6-3,7-6 |
| Challenger - Monterrey | 2023/02/20 19:30 | Nick Chappell v Maxime Mora | 6-4,6-3 |
| Challenger - Monterrey | 2023/02/19 21:00 | Nick Chappell v Cesar Ramirez | 7-6,6-2 |
| ATP - Dallas | 2023/02/05 23:10 | Brandon Holt v Nick Chappell | 6-3,6-2 |
| Challenger - Cleveland | 2023/01/30 23:35 | Nick Chappell v Mitchell Krueger | 3-6,6-7 |
| ITF - M15 Edmond | 2023/01/25 19:05 | Aidan Kim v Nick Chappell | 7-6,6-7,7-5 |
| ITF - M15 Ithaca | 2023/01/20 17:00 | Mac Kiger v Nick Chappell | 2-6,6-3,6-4 |
| ITF - M15 Ithaca | 2023/01/19 16:00 | Lucas Renard v Nick Chappell | 6-2,6-7,3-6 |
| ITF - M15 Ithaca | 2023/01/18 16:00 | Aman Sharma v Nick Chappell | 1-6,2-6 |
| Challenger - Monterrey | 2023/02/20 18:00 | Jorge Panta v Jesse Flores | 6-2,5-7,1-6 |
| Challenger - Monterrey | 2023/02/19 17:45 | Jesse Flores v Kristjan Tamm | 6-4,7-5 |
| ITF - M25 Santo Domingo | 2023/02/16 13:30 | Daniel Dutra Da Silva v Jesse Flores | 2-6,7-6,6-2 |
| ITF - M25 Santo Domingo | 2023/02/15 16:55 | Preston Brown v Jesse Flores | 2-6,2-6 |
| UTR Pro - Pozos | 2023/01/16 22:00 | Meethre Barot v Jesse Flores | 1-6,1-6 |
| UTR Pro - Pozos | 2023/01/14 18:00 | Ignacio Buse v Jesse Flores | 6-4,6-5 |
| UTR Pro - Pozos | 2023/01/13 22:00 | Anthony Wright v Jesse Flores | 6-4,2-6,3-5 |
| UTR Pro - Pozos | 2023/01/12 23:08 | Daniel Salazar v Jesse Flores | 3-6,6-7 |