Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| UTR Pro Florida | 2023/07/06 12:00 | Juan Sebastian Osorio v Sebastian Rondon | 7-6,6-1 |
| UTR Pro Florida | 2023/07/05 15:50 | Sylvestre Monnou v Juan Sebastian Osorio | 6-3,3-6,1-6 |
| UTR Pro Florida | 2023/07/04 12:00 | Dante Russo v Juan Sebastian Osorio | 1-6,4-6 |
| UTR Pro Florida | 2023/07/03 18:42 | Juan Sebastian Osorio v Matthis Ross | 6-3,4-6,3-6 |
| ITF M25 Santo Domingo | 2023/06/27 15:30 | Juan Sebastian Osorio v Joshua Lapadat | 1-6,1-6 |
| ITF M15 Santo Domingo | 2023/06/20 14:00 | Joshua Lapadat v Juan Sebastian Osorio | 7-5,1-6,6-4 |
| ITF M15 Tabasco | 2023/05/22 23:15 | Alan F R Fierros v Juan Sebastian Osorio | 6-1,6-2 |
| ITF M25 Xalapa | 2023/05/17 19:45 | Juan Sebastian Osorio v Ivar Jose Aramburu Contreras | 5-7,6-3,6-7 |
| ITF M25 Santo Domingo | 2023/06/29 13:30 | Tauheed Browning v Peter Bertran | 6-4,6-4 |
| ITF M25 Santo Domingo | 2023/06/28 17:10 | Elio Jose Ribeiro Lago v Peter Bertran | 7-6,0-6,2-6 |
| Davis Cup | 2023/06/24 19:35 | Daniel Phillips v Peter Bertran | 2-6,1-6 |
| Davis Cup | 2023/06/23 19:15 | Peter Bertran v Adolfo Daniel Vallejo | 2-6,2-6 |
| Davis Cup | 2023/06/22 20:00 | Peter Bertran v Jesse Flores | 5-7,3-6 |
| Davis Cup | 2023/06/20 19:55 | Peter Bertran v Alejandro Obando | 6-0,6-2 |
| Davis Cup | 2023/06/19 19:35 | Peter Bertran v Kevin Major | 6-4,6-3 |
| ITF M25 Wichita | 2023/06/16 14:45 | Ethan Quinn v Peter Bertran | 6-2,6-3 |