Stadium: Cancha 3 Round: 14 Ground: Clay
| Challenger Curitiba | 2023/10/23 13:00 | Gonzalo Villanueva v Gilbert S K Junior | 4-6,2-6 |
| ITF M15 Buenos Aires | 2023/09/01 12:50 | Gonzalo Villanueva v Gilbert S K Junior | 3-6,1-6 |
| Challenger Temuco | 2023/12/03 15:00 | Gilbert S K Junior v Aleksandar Kovacevic | 6-4,3-6,3-6 |
| Challenger Temuco | 2023/12/02 15:00 | Tomas Barrios Vera v Gilbert S K Junior | 4-6,3-6 |
| Challenger Temuco | 2023/12/01 14:00 | Gilbert S K Junior v Pedro Sakamoto | 6-0,6-3 |
| Challenger Temuco | 2023/11/29 17:00 | Ignacio Buse v Gilbert S K Junior | 4-6,6-7 |
| Challenger Temuco | 2023/11/27 17:35 | Gilbert S K Junior v Benjamin Lock | 6-3,6-2 |
| Challenger Brasilia | 2023/11/23 13:00 | Thiago Agustin Tirante v Gilbert S K Junior | 6-4,6-4 |
| Challenger Brasilia | 2023/11/21 20:05 | Wilson Leite v Gilbert S K Junior | 6-7,5-7 |
| Challenger Guayaquil | 2023/10/29 15:00 | Max Houkes v Gilbert S K Junior | 7-6,6-3 |
| Challenger Buenos Aires | 2024/01/09 20:05 | Oleksii Krutykh v Gonzalo Villanueva | 4-6,7-5,7-6 |
| Challenger Buenos Aires | 2024/01/08 15:15 | Adolfo Daniel Vallejo v Gonzalo Villanueva | 2-6,4-6 |
| Challenger Buenos Aires | 2024/01/07 13:00 | Vito Antonio Darderi v Gonzalo Villanueva | 1-6,0-6 |
| ITF M15 Concepcion | 2023/12/16 13:00 | Gonzalo Villanueva v Facundo Mena | 6-3,6-4 |
| ITF M15 Concepcion | 2023/12/15 13:00 | Gonzalo Villanueva v Ignacio A B Otarola | 6-0,6-1 |
| ITF M15 Concepcion | 2023/12/14 16:05 | Gonzalo Villanueva v Diego F Flores | 6-0,7-6 |
| ITF M15 Concepcion | 2023/12/13 15:05 | Gonzalo Villanueva v Miguel Angel Cabrera | 6-3,6-1 |
| ITF M15 Concepcion | 2023/12/11 18:00 | Gonzalo Villanueva v Fernando Cavallo | 6-2,6-0 |