Stadium: Cancha 4 Round: 24 Ground: Clay
| ITF Argentina F6 | 2017/09/06 13:00 | Mariano Kestelboim v Oscar Jose Gutierrez | 6-0,1-6,6-4 |
| Montevideo, Uruguay | 2019/11/05 16:15 | Genaro Alberto Olivieri v Oscar Jose Gutierrez | 5-7,6-3,6-4 |
| Challenger Guayaquil | 2019/10/30 23:15 | Jaume Munar v Oscar Jose Gutierrez | 6-4,6-2 |
| Challenger Guayaquil | 2019/10/28 18:15 | Pedro Sakamoto v Oscar Jose Gutierrez | 6-3,6-7,4-6 |
| Challenger - Lima | 2019/10/23 00:55 | Oscar Jose Gutierrez v Yannick Hanfmann | 3-6,3-6 |
| Challenger - Lima | 2019/10/22 01:25 | Nicolas Alvarez v Oscar Jose Gutierrez | 3-6,3-6 |
| Santo Domingo, Dominican Republic | 2019/10/10 19:00 | Thiago Monteiro v Oscar Jose Gutierrez | 6-3,7-5 |
| Santo Domingo, Dominican Republic | 2019/10/08 22:55 | Oscar Jose Gutierrez v Krstin, Pedja | 7-5,6-4 |
| Challenger Campinas | 2019/09/30 18:05 | Oscar Jose Gutierrez v Juan Pablo Varillas | 2-6,2-6 |
| Maldonado, Singles Qualifying M-ITF-URU-01A | 2019/12/01 13:00 | Santiago Rodriguez Taverna v Mariano Kestelboim | 3-6,6-2,6-1 |
| Maldonado, Singles Qualifying M-ITF-URU-01A | 2019/11/30 13:30 | Francisco Comesana v Mariano Kestelboim | 5-7,3-6 |
| Maldonado, Singles Qualifying M-ITF-URU-01A | 2019/11/29 13:00 | Franco Emanuel Egea v Mariano Kestelboim | 4-6,3-6 |
| Maldonado, Singles Qualifying M-ITF-URU-01A | 2019/11/28 15:00 | Nicolas Bruna v Mariano Kestelboim | 2-6,6-3,0-6 |
| Maldonado, Singles Qualifying M-ITF-URU-01A | 2019/11/26 13:30 | Bruna, Esteban v Mariano Kestelboim | 4-6,2-6 |
| ITF M15 Cancun | 2019/11/19 14:00 | Mariano Kestelboim v Farren, Connor | 3-6,4-6 |
| ITF M15 Cancun | 2019/11/16 18:50 | Hank, Tigre v Mariano Kestelboim | 3-6,6-3,6-4 |
| ITF M15 Cancun | 2019/11/16 13:45 | Patino, Luis v Mariano Kestelboim | 2-6,7-5,1-6 |