Stadium: Court 1 Round: 26 Ground: Clay
| ITF M15 Bucharest | 2023/08/30 10:25 | Jesse Flores v Dragos N Cazacu | 6-3,7-6 |
| ITF M15 Pittsburgh | 2023/07/28 14:50 | Jesse Flores v Juan Carlos Aguilar | 6-4,1-6,3-6 |
| ITF M15 Pittsburgh | 2023/07/27 17:40 | William Grant v Jesse Flores | 6-4,2-6,4-6 |
| ITF M15 Pittsburgh | 2023/07/26 15:50 | Alex Bancila v Jesse Flores | 4-6,5-7 |
| ITF M15 Rochester | 2023/07/20 18:25 | Ignacio Monzon v Jesse Flores | 7-6,4-6,6-4 |
| ITF M15 Rochester | 2023/07/19 17:00 | Jesse Flores v Emmett Ward | 6-2,6-2 |
| Davis Cup | 2023/06/24 19:35 | Jesse Flores v Ricardo Rodriguez-Pace | 6-2,7-6 |
| Davis Cup | 2023/06/23 19:15 | Jesse Flores v Alejandro Obando | 6-2,6-2 |
| ITF M15 Bucharest | 2023/08/30 09:15 | Gian Marco Ortenzi v Ioan Alexandru Chirita | 6-1,6-4 |
| ITF M15 Bucharest | 2023/08/29 06:30 | Gian Marco Ortenzi v Leonardo Taddia | 6-1,6-2 |
| ITF M15 Bucharest | 2023/08/28 06:30 | Gian Marco Ortenzi v Facundo Bermejo | 6-2,6-1 |
| ITF M15 Bucharest | 2023/08/27 06:00 | Gian Marco Ortenzi v Daniel Uta | 6-2,6-3 |
| ITF M25 Lesa | 2023/08/21 10:55 | Nikola Basic v Gian Marco Ortenzi | 6-7,3-6 |
| ITF M25 Lesa | 2023/08/20 08:00 | Lorenzo Beraldo v Gian Marco Ortenzi | 4-6,6-7 |
| ITF M15 Gubbio | 2023/07/19 12:10 | Fausto Tabacco v Gian Marco Ortenzi | 6-3,5-7,6-1 |
| ITF M15 Gubbio | 2023/07/17 12:00 | Federico Campana v Gian Marco Ortenzi | 4-6,6-3,6-10 |