Stadium: Court 9 Round: 25 Ground: Clay
| Challenger Vina del Mar | 2023/03/14 17:25 | Andrea Pellegrino v Gonzalo Villanueva | 6-0,6-2 |
| Challenger Vina del Mar | 2023/03/13 14:00 | Gonzalo Villanueva v Wilson Leite | 3-6,3-6 |
| Challenger Vina del Mar | 2023/03/12 13:00 | Gonzalo Villanueva v Bor Artnak | 6-7,6-4,6-2 |
| Challenger Santiago | 2023/03/07 18:55 | Gonzalo Villanueva v Hernan Casanova | 0-6,1-6 |
| Challenger Santiago | 2023/03/06 14:55 | Gonzalo Villanueva v Federico Gaio | 4-6,4-6 |
| Challenger Santiago | 2023/03/05 15:35 | Gonzalo Villanueva v Ignacio A B Otarola | 6-2,6-0 |
| ATP Acapulco | 2023/02/26 03:45 | Rubin Statham v Gonzalo Villanueva | 6-3,6-2 |
| ITF M25 Santo Domingo | 2023/02/24 14:00 | Kyle Seelig v Gonzalo Villanueva | 6-3,4-6,6-3 |
| ITF M15 Santo Domingo | 2023/04/11 16:00 | Mateo Barreiros Reyes v Miguel Angel Cabrera | 6-1,3-6,5-10 |
| ITF M15 Santo Domingo | 2023/04/10 14:00 | Mateo Barreiros Reyes v Ryan A Dos Santos | 6-2,6-3 |
| ITF M15 De Los Tsachilas | 2023/04/06 17:15 | Alvaro Guillen Meza v Mateo Barreiros Reyes | 6-1,6-4 |
| ITF M15 De Los Tsachilas | 2023/04/05 19:05 | Mateo Barreiros Reyes v Daniel Antonio Nunez | 6-4,6-4 |
| ITF M15 Santo Domingo | 2023/04/04 14:00 | Mateo Barreiros Reyes v Jaycer Lyeons | 6-2,7-5 |
| ITF M15 Santo Domingo | 2023/04/03 14:00 | Mateo Barreiros Reyes v Miguel Fernando Pereira | 6-1,6-2 |
| ITF M25 Mosquera | 2023/03/20 20:20 | Ryan A Dos Santos v Mateo Barreiros Reyes | 4-6,6-4,15-13 |
| ITF M25 Anapoima | 2023/03/16 20:05 | Mateo Barreiros Reyes v Elmar Ejupovic | 3-6,3-6 |