Stadium: Court 1 Round: 27 Ground: Clay
| 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 |
| ITF M15 Concepcion | 2023/12/08 14:00 | Gonzalo Villanueva v Nicolas Kicker | 3-6,7-6,3-6 |
| ITF M15 Concepcion | 2023/12/07 16:35 | Gonzalo Villanueva v Manuel Mouilleron Salvo | 6-1,7-6 |
| ITF M15 Concepcion | 2023/12/05 14:00 | Gonzalo Villanueva v Nicolas Villalon | 6-1,6-3 |
| Challenger Temuco | 2023/11/29 15:00 | Gonzalo Villanueva v Aleksandar Kovacevic | 4-6,6-7 |
| Challenger Temuco | 2023/11/27 19:20 | Rubin Statham v Gonzalo Villanueva | 3-6,3-6 |
| Challenger Montevideo | 2023/11/12 18:20 | Santiago Rodriguez Taverna v Gonzalo Villanueva | 7-5,7-5 |
| ITF M15 Concepcion | 2023/12/13 14:35 | Diego F Flores v Juan Pablo Paz | 6-4,4-6,6-3 |
| ITF M15 Concepcion | 2023/12/11 14:30 | Diego F Flores v Joao Victor C Loureiro | 6-4,6-3 |
| ITF M15 Concepcion | 2023/12/08 14:00 | Facundo Mena v Diego F Flores | 6-2,6-0 |
| ITF M15 Concepcion | 2023/12/07 14:00 | Diego F Flores v Nicolas Zanellato | 6-4,4-6,7-5 |
| ITF M15 Concepcion | 2023/12/06 16:15 | Diego F Flores v Benjamin Herrera | 6-3,6-2 |
| ITF M15 Concepcion | 2023/12/04 14:30 | Diego F Flores v Felipe De Dios | 6-3,6-4 |
| ITF M15 Concepcion | 2023/12/03 17:30 | Diego F Flores v Benjamin Zuniga Garcia | 6-3,6-2 |
| Challenger Temuco | 2023/11/28 16:00 | Tomas Barrios Vera v Diego F Flores | 6-1,6-2 |