Round: 25 Ground: Clay
| ITF Chile F5 | 2016/12/12 14:00 | Leonardo Aboian v Gustavo De O Cruz | 5-7,4-6 |
| ITF Chile F6 | 2016/12/04 15:00 | Leonardo Aboian v Gustavo De O Cruz | 6-3,6-4 |
| ITF Chile F6 | 2016/12/03 14:00 | Nikolas Papic v Gustavo De O Cruz | 2-6,1-6 |
| ITF Chile F5 | 2016/11/27 16:00 | Gustavo De O Cruz v Santiago Besada | 3-6,1-6 |
| ITF Bolivia F3 | 2016/11/22 21:20 | Fabrizio Ornago v Gustavo De O Cruz | 7-6,6-0 |
| ITF Bolivia F3 Qual | 2016/11/20 14:00 | Gustavo De O Cruz v Alan Postay | 6-4,6-2 |
| ITF Bolivia F2 Qual | 2016/11/13 14:00 | Gustavo De O Cruz v Nicolas Bacella | 3-6,6-3,3-6 |
| ITF Bolivia F1 | 2016/11/06 16:30 | Gustavo De O Cruz v Javier Gonzalez | 4-6,6-7 |
| ITF Chile F6 | 2016/12/06 14:00 | Fernando Yamacita v Cristobal S-Corvalan | 6-3,7-6 |
| ITF Chile F5 | 2016/11/30 17:15 | Genaro Alberto Olivieri v Cristobal S-Corvalan | 6-2,6-3 |
| ITF Chile F5 | 2016/11/29 13:10 | Fernando Yamacita v Cristobal S-Corvalan | 1-6,6-3,4-6 |
| ITF Bolivia F3 | 2016/11/24 22:20 | Cristobal S-Corvalan v Matias Zukas | 4-6,7-6,7-6 |
| ITF Bolivia F3 | 2016/11/23 21:00 | Cristobal S-Corvalan v Mauricio Echazu | 3-6,6-2,6-3 |
| ITF Bolivia F3 | 2016/11/22 19:00 | Cristobal S-Corvalan v Genaro Alberto Olivieri | 4-6,7-5,6-2 |
| Challenger Montevideo Qual | 2016/11/12 15:00 | Rodrigo Arus v Cristobal S-Corvalan | 6-4,6-4 |
| ITF Argentina F13 | 2016/11/08 14:15 | Franco Emanuel Egea v Cristobal S-Corvalan | 6-4,6-3 |