Stadium: Cancha 6 Round: 24 Ground: Clay
| Santo Domingo, Dominican Republic | 2019/10/08 22:55 | Oscar Jose Gutierrez v Krstin, Pedja | 7-5,6-4 |
| Challenger Sibiu | 2019/09/19 11:40 | Krstin, Pedja v Blaz Rola | 1-6,6-3,1-6 |
| Challenger Sibiu | 2019/09/18 07:00 | Krstin, Pedja v Dembek, Michal | 6-4,6-2 |
| Challenger Banja Luka | 2019/09/14 11:00 | Tallon Griekspoor v Krstin, Pedja | 6-4,4-6,7-5 |
| Challenger Banja Luka | 2019/09/13 14:00 | Dmitry Popko v Krstin, Pedja | 4-6,4-6 |
| Challenger Banja Luka | 2019/09/12 09:45 | Krstin, Pedja v Berlocq, Carlos | 6-2,6-4 |
| Challenger Banja Luka | 2019/09/11 08:00 | Krstin, Pedja v Balzerani, Riccardo | 6-2,6-4 |
| Jinan, China | 2019/09/04 04:20 | Chun Hsin Tseng v Krstin, Pedja | 7-6,7-6 |
| Santo Domingo, Dominican Republic | 2019/10/08 23:00 | Gonzalo Villanueva v Hugo Dellien | 2-6,3-6 |
| Santo Domingo, Dominican Republic | 2019/10/07 19:00 | Gonzalo Villanueva v Molteni, Andres | 4-6,6-4,6-2 |
| Challenger Campinas | 2019/10/02 15:20 | Gonzalo Villanueva v Alejandro Tabilo | 0-6,3-6 |
| Challenger Campinas | 2019/10/01 13:00 | Gonzalo Villanueva v Romboli, Fernando | 6-2,6-2 |
| Challenger - Buenos Aires | 2019/09/24 14:00 | Federico Zeballos v Gonzalo Villanueva | 6-4,6-1 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2019/09/22 16:50 | Estevez Maximiliano v Gonzalo Villanueva | 6-4,4-6,1-6 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2019/09/21 16:40 | Genaro Alberto Olivieri v Gonzalo Villanueva | 4-6,3-6 |
| Buenos Aires, Singles Qualifying M-ITF-ARG-22A | 2019/09/20 15:00 | Facundo Diaz Acosta v Gonzalo Villanueva | 5-7,1-6 |