Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger - Segovia | 2019/07/29 09:50 | Artem Dubrivnyy v Julian Ocleppo | 6-7,6-4,2-6 |
| ATP - Båstad | 2019/07/14 08:30 | Julian Ocleppo v Alexey Vatutin | 2-6,2-6 |
| Challenger - Perugia | 2019/07/08 15:35 | Aldin Setkic v Julian Ocleppo | 6-4,6-3 |
| ITF M25 Cuneo | 2019/07/05 12:45 | Jose Hernandez-Fernandez v Julian Ocleppo | 6-0,6-2 |
| ITF M25 Cuneo | 2019/07/04 10:50 | Andrea Gola v Julian Ocleppo | 6-4,0-6,6-7 |
| ITF M25 Cuneo | 2019/07/02 16:00 | Nicola Cigna v Julian Ocleppo | 7-6,1-6,4-6 |
| Challenger - Milan | 2019/06/26 08:00 | Julian Ocleppo v Pedro Sousa | 3-6,5-7 |
| Challenger - Milan | 2019/06/24 15:50 | Raul Brancaccio v Julian Ocleppo | 1-6,6-3,5-7 |
| 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 - Winnipeg | 2019/07/11 20:00 | Cem Ilkel v Roberto Ortega-Olmedo | 7-6,6-3 |
| Challenger - Winnipeg | 2019/07/10 16:40 | Roberto Ortega-Olmedo v Dudi Sela | 6-4,6-2 |
| Challenger - Winnipeg | 2019/07/08 21:00 | Evan Song v Roberto Ortega-Olmedo | 1-6,4-6 |
| ITF M25 - Bakio | 2019/07/04 10:30 | Roberto Ortega-Olmedo v Laurent Lokoli | 3-6,5-7 |
| ITF M25 - Bakio | 2019/07/03 16:00 | Roberto Ortega-Olmedo v Hendrik Jebens | 6-1,6-4 |
| ATP - Antalya | 2019/06/23 10:30 | Viktor Troicki v Roberto Ortega-Olmedo | 3-6,7-6,6-2 |