Stadium: Yonex Court Round: 27 Ground: Clay
| Challenger Leon | 2019/04/23 20:00 | Pedja Krstin v Roberto Ortega-Olmedo | 7-6,6-3 |
| Challenger Meerbusch | 2019/08/15 10:30 | Roberto Ortega-Olmedo v Raul Brancaccio | 6-4,6-7,6-4 |
| Challenger Meerbusch | 2019/08/14 09:20 | Roberto Ortega-Olmedo v Adam Pavlasek | 6-3,6-4 |
| ITF M25 Pozoblanco | 2019/08/08 18:00 | Roberto Ortega-Olmedo v Mick Lescure | 6-4,3-6,4-6 |
| ITF M25 Pozoblanco | 2019/08/07 18:10 | Roberto Ortega-Olmedo v Artem Dubrivnyy | 6-4,6-4 |
| Challenger Segovia | 2019/08/01 10:00 | Markus Eriksson v Roberto Ortega-Olmedo | 1-6,6-1,7-5 |
| Challenger Segovia | 2019/07/31 10:35 | Julian Ocleppo v Roberto Ortega-Olmedo | 7-6,3-6,4-6 |
| Challenger Binghamton | 2019/07/24 19:20 | Yuichi Sugita v Roberto Ortega-Olmedo | 7-5,6-1 |
| Challenger Gatineau | 2019/07/15 21:30 | Roberto Ortega-Olmedo v Skander Mansouri | 1-6,4-6 |
| Challenger Meerbusch | 2019/08/15 11:05 | Facundo Mena v Pedja Krstin | 2-6,0-6 |
| Challenger Meerbusch | 2019/08/14 11:15 | Lucas Gerch v Pedja Krstin | 1-6,4-6 |
| ATP Kitzbuhel | 2019/07/27 11:30 | Hugo Dellien v Pedja Krstin | 6-3,7-5 |
| Challenger Tampere | 2019/07/26 13:55 | Pedja Krstin v Mikael Ymer | 6-2,1-6,6-7 |
| Challenger Tampere | 2019/07/25 09:00 | Guilherme Clezar v Pedja Krstin | 6-7,1-6 |
| Challenger Tampere | 2019/07/24 11:15 | Christopher O'Connell v Pedja Krstin | 4-6,6-1,3-6 |
| Challenger San Benedetto | 2019/07/16 13:05 | Pedja Krstin v Oriol Roca Batalla | 3-6,6-7 |
| Challenger Perugia | 2019/07/10 15:15 | Pedja Krstin v Daniel Elahi Galan | 1-6,6-7 |