Stadium: Cancha 2 Round: 27 Ground: Hardcourt outdoor
| Challenger – Sao Paulo | 2021/11/30 12:30 | Pedro Sakamoto v Gilbert S K Junior | 2-6,7-5,7-5 |
| ITF M25 Medellin | 2021/09/18 14:50 | Pedro Sakamoto v Gilbert S K Junior | 3-6,6-7 |
| 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 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 Temuco | 2023/11/29 18:40 | Joao Lucas Reis da Silva v Pedro Sakamoto | 4-6,6-4,2-6 |
| Challenger Temuco | 2023/11/28 13:00 | Pedro Sakamoto v Juan Pablo Ficovich | 5-7,7-6,6-4 |
| Challenger - Brasilia | 2023/11/22 15:00 | Juan Pablo Ficovich v Pedro Sakamoto | 6-1,6-2 |
| Challenger - Brasilia | 2023/11/20 14:00 | Pedro Sakamoto v Juan Pablo Paz | 7-6,6-4 |
| Challenger - Brasilia | 2023/11/19 13:00 | Pedro Sakamoto v Gabriel Decamps | 6-1,3-6,7-6 |
| Challenger - Montevideo | 2023/11/16 17:00 | Facundo Diaz Acosta v Pedro Sakamoto | 6-1,6-2 |
| Challenger - Montevideo | 2023/11/14 15:00 | Franco Agamenone v Pedro Sakamoto | 4-6,1-6 |
| Challenger - Montevideo | 2023/11/13 15:00 | Valentin Vacherot v Pedro Sakamoto | 3-6,0-6 |