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