Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
| Challenger Bogota | 2023/09/25 15:00 | Wilson Leite v Gilbert S K Junior | 3-6,6-7 |
| ITF M15 Plovdiv | 2019/06/06 07:00 | Gilbert S K Junior v Wilson Leite | 7-6,3-6,7-5 |
| Challenger Brasilia | 2023/11/20 15:35 | Gonzalo Lama v Wilson Leite | 6-7,5-7 |
| Challenger Brasilia | 2023/11/19 17:05 | Adam Taylor v Wilson Leite | 6-7,2-6 |
| Challenger Montevideo | 2023/11/12 16:45 | Murkel Dellien v Wilson Leite | 6-1,6-3 |
| Challenger Guayaquil | 2023/10/29 19:05 | Carlos Taberner v Wilson Leite | 3-6,7-5,6-1 |
| Challenger Curitiba | 2023/10/25 21:30 | Wilson Leite v Santiago Rodriguez Taverna | 6-7,4-6 |
| Challenger Curitiba | 2023/10/23 17:00 | Juan Manuel Cerundolo v Wilson Leite | 3-6,5-7 |
| ITF M25 Lajeado | 2023/10/15 13:50 | Pedro Sakamoto v Wilson Leite | 6-1,6-1 |
| ITF M25 Lajeado | 2023/10/14 17:05 | Wilson Leite v Leonardo Aboian | 2-6,6-3,6-4 |
| Challenger Guayaquil | 2023/10/29 15:00 | Max Houkes v Gilbert S K Junior | 7-6,6-3 |
| Challenger Curitiba | 2023/10/24 16:15 | Gilbert S K Junior v Guido Andreozzi | 2-6,0-6 |
| Challenger Curitiba | 2023/10/23 13:00 | Gonzalo Villanueva v Gilbert S K Junior | 4-6,2-6 |
| 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 |