Stadium: Quadra 1 Round: 19 Ground: Clay
| ITF M15 Buenos Aires | 2023/09/01 12:50 | Gonzalo Villanueva v Gilbert S K Junior | 3-6,1-6 |
| Challenger Curitiba | 2023/10/22 13:00 | Gonzalo Villanueva v Kaua Lorenzo Santos Gava | 6-2,6-0 |
| Challenger Santa Fe | 2023/10/16 15:40 | Carlos Taberner v Gonzalo Villanueva | 6-1,6-4 |
| Challenger Santa Fe | 2023/10/15 16:35 | Gonzalo Villanueva v Alvaro Guillen Meza | 6-3,4-6,6-3 |
| Challenger Buenos Aires | 2023/10/12 15:35 | Franco Agamenone v Gonzalo Villanueva | 7-6,6-2 |
| Challenger Buenos Aires | 2023/10/10 17:35 | Gonzalo Villanueva v Juan Bautista Torres | 2-6,6-2,6-3 |
| Challenger Buenos Aires | 2023/10/09 14:00 | Alex Barrena v Gonzalo Villanueva | 4-6,3-6 |
| Challenger Buenos Aires | 2023/10/08 13:00 | Gonzalo Villanueva v Nicolas Mejia | 6-4,6-2 |
| ITF M25 Mendoza | 2023/10/06 15:35 | Gonzalo Villanueva v Luciano Emanuel Ambrogi | 3-6,4-6 |
| Challenger Curitiba | 2023/10/22 14:45 | Gabriel Roveri Sidney v Gilbert S K Junior | 0-6,1-6 |
| Challenger Campinas | 2023/10/01 13:00 | Paulo A S Dos Santos v Gilbert S K Junior | 2-6,6-4,6-4 |
| Challenger Bogota | 2023/09/28 15:00 | Tomas Barrios Vera v Gilbert S K Junior | 6-2,3-6,7-6 |
| Challenger Bogota | 2023/09/26 17:10 | Gilbert S K Junior v Matias Soto | 6-4,6-2 |
| Challenger Bogota | 2023/09/25 15:00 | Wilson Leite v Gilbert S K Junior | 3-6,6-7 |
| Challenger Bogota | 2023/09/24 17:50 | Juan Sebastian Gomez v Gilbert S K Junior | 2-6,4-6 |
| Challenger Antofagasta | 2023/09/19 13:00 | Hugo Dellien v Gilbert S K Junior | 6-2,6-0 |
| Challenger Antofagasta | 2023/09/18 13:00 | Gilbert S K Junior v Juan Bautista Otegui | 6-1,6-1 |