Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sunrise | 2023/04/11 21:00 | Jesse Flores v Kaylan Bigun | 1-6,4-6 |
| UTR Pro Florida | 2023/03/27 21:15 | Felipe Pinzon Moreno v Jesse Flores | 3-6,7-5,1-6 |
| ITF M25 Montreal | 2023/03/14 16:55 | Jesse Flores v Joe Tyler | 1-6,3-6 |
| ITF M25 Montreal | 2023/03/13 13:55 | Jesse Flores v Ren Nakamura | 6-2,6-1 |
| ITF M25 Montreal | 2023/03/06 14:55 | Jesse Flores v Jean-Christian Morandais | 6-2,6-7,7-10 |
| Challenger Monterrey | 2023/02/21 23:20 | Nick Chappell v Jesse Flores | 6-3,6-2 |
| 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 M15 Tacarigua | 2023/04/17 18:00 | Aurel Ciocanu v Matthew Foster-Estwick | 2-6,7-5,6-10 |
| ITF M15 Tacarigua | 2023/04/16 21:30 | Tony Bourcet v Matthew Foster-Estwick | 2-6,2-6 |
| ITF M15 Sunrise | 2023/04/11 23:00 | Elio Jose Ribeiro Lago v Matthew Foster-Estwick | 6-3,6-0 |
| ITF M15 Sunrise | 2023/04/11 16:00 | Rodrigo Reyna v Matthew Foster-Estwick | 3-6,3-6 |
| ITF M25 Wesley Chapel | 2023/01/24 15:45 | Connor Farren v Matthew Foster-Estwick | 6-2,6-0 |
| ITF M25 Wesley Chapel | 2023/01/23 14:45 | Khaleel Gbedey v Matthew Foster-Estwick | 2-6,2-6 |
| ITF M15 Ithaca | 2023/01/17 16:00 | Aman Sharma v Matthew Foster-Estwick | 6-4,6-2 |
| ITF M15 Santo Domingo | 2022/11/30 13:30 | Matthew Foster-Estwick v Andrei Duarte | 7-6,4-6,5-7 |