Stadium: Pista 2 Round: 25 Ground: Hardcourt outdoor
| 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 Winnipeg | 2019/07/11 20:00 | Cem Ilkel v Ortega-Olmedo, Roberto | 7-6,6-3 |
| Challenger Winnipeg | 2019/07/10 16:40 | Ortega-Olmedo, Roberto v Sela, Dudi | 6-4,6-2 |
| Challenger Winnipeg | 2019/07/08 21:00 | Song, Evan v Ortega-Olmedo, Roberto | 1-6,4-6 |
| ITF M25 Bakio | 2019/07/04 10:30 | Ortega-Olmedo, Roberto v Laurent Lokoli | 3-6,5-7 |
| Segovia, Spain | 2019/07/29 09:50 | Dubrivnyy, Artem v Ocleppo, Julian | 6-7,6-4,2-6 |
| Piestany, Singles M-ITF-SVK-02A | 2019/07/20 08:00 | Dubrivnyy, Artem v Fabian Marozsan | 7-5,3-6,1-6 |
| Piestany, Singles M-ITF-SVK-02A | 2019/07/19 08:00 | Melnic, Vladislav v Dubrivnyy, Artem | 7-6,4-6,4-6 |
| Piestany, Singles M-ITF-SVK-02A | 2019/07/18 10:00 | Oleksii Krutykh v Dubrivnyy, Artem | 2-6,2-6 |
| Piestany, Singles M-ITF-SVK-02A | 2019/07/17 11:35 | Yvo Panak v Dubrivnyy, Artem | 1-6,4-6 |
| ITF M15 Belgrade | 2019/07/04 10:15 | Gergely Madarasz v Dubrivnyy, Artem | 6-4,6-4 |
| ITF M15 Belgrade | 2019/07/03 08:00 | Micov, Stefan v Dubrivnyy, Artem | 5-7,6-7 |
| Balatonalmadi, Singles Qualifying M-ITF-HUN-02A | 2019/06/22 10:00 | Gergely Madarasz v Dubrivnyy, Artem | 5-7,7-5,6-4 |