Stadium: Pista 4 Round: 14 Ground: Clay
| Challenger Vina del Mar | 2023/03/13 14:00 | Daniel Dutra Da Silva v Jose Pereira | 6-7,5-7 |
| Challenger Vina del Mar | 2023/03/12 13:00 | Daniel Dutra Da Silva v Benjamin Torres | 6-1,6-2 |
| Challenger Santiago | 2023/03/06 13:00 | Daniel Dutra Da Silva v Jose Pereira | 6-4,6-4 |
| Challenger Santiago | 2023/03/05 13:00 | Daniel Dutra Da Silva v Francisco Duran | 6-2,6-2 |
| ITF M25 Santo Domingo | 2023/02/24 16:15 | Adam Walton v Daniel Dutra Da Silva | 6-3,6-1 |
| ITF M25 Santo Domingo | 2023/02/23 15:55 | Ezekiel Clark v Daniel Dutra Da Silva | 3-6,3-6 |
| ITF M25 Santo Domingo | 2023/02/22 18:30 | Miles Jones v Daniel Dutra Da Silva | 6-7,6-7 |
| ITF M25 Santo Domingo | 2023/02/19 13:55 | Daniel Dutra Da Silva v Kyle Seelig | 7-6,7-5 |
| Challenger Vina del Mar | 2023/03/17 21:35 | Tomas Barrios Vera v Alvaro Lopez San Martin | 7-5,6-4 |
| Challenger Vina del Mar | 2023/03/16 14:00 | Juan Bautista Torres v Alvaro Lopez San Martin | 6-4,4-6,2-6 |
| Challenger Vina del Mar | 2023/03/14 16:30 | Alvaro Lopez San Martin v Luciano Darderi | 6-2,5-7,6-1 |
| Challenger Vina del Mar | 2023/03/13 16:15 | Alvaro Lopez San Martin v Lorenzo Bocchi | 6-3,6-2 |
| Challenger Vina del Mar | 2023/03/12 18:10 | Alvaro Lopez San Martin v Cristobal Castro | 6-0,6-0 |
| Challenger Santiago | 2023/03/07 16:25 | Genaro Alberto Olivieri v Alvaro Lopez San Martin | 7-6,6-4 |
| Challenger Santiago | 2023/03/06 15:00 | Alvaro Lopez San Martin v Wilson Leite | 6-2,6-2 |
| Challenger Santiago | 2023/03/05 16:45 | Alvaro Lopez San Martin v Marcelo Zormann | 6-4,7-6 |