Round: 25 Ground: Clay
| ITF Argentina F7 | 2015/05/23 12:00 | Oscar Jose Gutierrez v Alejo Vilaro | 6-2,6-3 |
| ITF Colombia F9 | 2016/12/01 15:00 | Ivan Endara v Oscar Jose Gutierrez | 6-2,7-5 |
| ITF Colombia F9 | 2016/11/30 16:45 | Alejandro H Franco v Oscar Jose Gutierrez | 1-6,0-6 |
| ITF Colombia F9 | 2016/11/28 18:00 | Aaron Cortes Alcaraz v Oscar Jose Gutierrez | 6-7,2-6 |
| ITF Colombia F8 | 2016/11/23 14:30 | Daniel Elahi Galan v Oscar Jose Gutierrez | 4-6,6-1,7-6 |
| ITF Colombia F8 | 2016/11/22 16:20 | Juan Montes v Oscar Jose Gutierrez | 0-6,1-6 |
| ITF Colombia F7 | 2016/11/18 15:00 | Juan Pablo Varillas v Oscar Jose Gutierrez | 2-6,6-3,6-4 |
| ITF Colombia F7 | 2016/11/17 15:00 | Oscar Jose Gutierrez v Carlos Salamanca | 5-7,6-3,6-1 |
| ITF Colombia F7 | 2016/11/16 15:00 | Oscar Jose Gutierrez v Camilo Andres Erazo | 6-1,6-2 |
| ITF Uruguay F1 | 2016/11/30 16:50 | Gonzalo Villanueva v Alejo Vilaro | 6-3,6-2 |
| ITF Uruguay F1 | 2016/11/28 13:00 | Alejo Vilaro v Ignacio Carou | 6-3,6-1 |
| Challenger Montevideo Qual | 2016/11/12 13:00 | Alejo Vilaro v Dario Acosta | 4-6,3-6 |
| ITF Argentina F13 | 2016/11/07 12:00 | Alejo Vilaro v Juan Ignacio Ameal | 6-7,5-7 |
| ITF Argentina F13 | 2016/11/06 15:25 | Alejo Vilaro v Marco Pairetti | 6-0,6-0 |
| ITF Argentina F12 Qual | 2016/10/28 22:00 | Sebastian Baez v Alejo Vilaro | 6-2,1-6,6-4 |
| ITF Argentina F11 Qual | 2016/10/23 15:30 | Alejo Vilaro v Juan Bautista Otegui | 7-6,4-6,3-6 |
| Challenger Buenos Aires 2 Qual | 2016/10/08 15:10 | Axel Geller v Alejo Vilaro | 7-5,6-7,6-3 |