Stadium: Estadio 2 Round: 25 Ground: Clay
| Challenger Campinas | 2019/09/30 18:05 | Oscar Jose Gutierrez v Juan Pablo Varillas | 2-6,2-6 |
| Challenger Buenos Aires | 2019/09/23 15:10 | Genaro Alberto Olivieri v Oscar Jose Gutierrez | 6-4,6-4 |
| Challenger Biella | 2019/09/18 08:00 | Tommy Robredo v Oscar Jose Gutierrez | 6-0,6-1 |
| Challenger Biella | 2019/09/17 08:00 | Gianluigi Quinzi v Oscar Jose Gutierrez | 2-6,6-1,3-6 |
| Challenger Szczecin | 2019/09/09 14:30 | Oscar Jose Gutierrez v Jan Satral | 6-7,3-6 |
| ITF M25 - Donostia-San-Sebastian | 2019/09/01 10:30 | Oscar Jose Gutierrez v Javier Barranco Cosano | 5-7,0-6 |
| ITF M25 - Donostia-San-Sebastian | 2019/08/31 11:20 | Oscar Jose Gutierrez v Orlando Luz | 6-2,6-3 |
| ITF M25 - Donostia-San-Sebastian | 2019/08/30 10:35 | Jose Hernandez-Fernandez v Oscar Jose Gutierrez | 3-6,4-6 |
| Challenger Sibiu | 2019/09/19 11:40 | Pedja Krstin v Blaz Rola | 1-6,6-3,1-6 |
| Challenger Sibiu | 2019/09/18 07:00 | Pedja Krstin v Michal Dembek | 6-4,6-2 |
| Challenger Banja Luka | 2019/09/14 11:00 | Tallon Griekspoor v Pedja Krstin | 6-4,4-6,7-5 |
| Challenger Banja Luka | 2019/09/13 14:00 | Dmitry Popko v Pedja Krstin | 4-6,4-6 |
| Challenger Banja Luka | 2019/09/12 09:45 | Pedja Krstin v Carlos Berlocq | 6-2,6-4 |
| Challenger Banja Luka | 2019/09/11 08:00 | Pedja Krstin v Riccardo Balzerani | 6-2,6-4 |
| Challenger Jinan | 2019/09/04 04:20 | Chun Hsin Tseng v Pedja Krstin | 7-6,7-6 |
| Challenger Baotou | 2019/08/29 08:55 | Pedja Krstin v Runhao Hua | 6-4,6-2 |