Stadium: Central A.Berasategi Round: 25 Ground: Hardcourt outdoor
| Challenger Las Vegas Qual | 2016/10/16 19:45 | Roberto Ortega-Olmedo v Hendrik Jebens | 6-0,6-1 |
| ATP Antalya | 2019/06/23 10:30 | Viktor Troicki v Roberto Ortega-Olmedo | 3-6,7-6,6-2 |
| ATP Antalya | 2019/06/22 11:35 | Roberto Ortega-Olmedo v Mukund Sasikumar | 6-2,6-1 |
| Challenger Blois | 2019/06/18 09:20 | Roberto Ortega-Olmedo v Pedro Cachin | 0-6,2-6 |
| Challenger Blois | 2019/06/17 11:40 | Roberto Ortega-Olmedo v Kenny de Schepper | 6-3,6-4 |
| Challenger Lyon | 2019/06/10 10:45 | Roberto Ortega-Olmedo v Elliot Benchetrit | 1-6,5-7 |
| Challenger Poznan | 2019/06/04 12:35 | Roberto Ortega-Olmedo v Dennis Novak | 0-6,4-6 |
| Challenger Poznan | 2019/06/03 12:15 | Roberto Ortega-Olmedo v Javier Barranco Cosano | 6-3,6-7,6-4 |
| Challenger Jerusalem | 2019/05/23 07:00 | Brayden Schnur v Roberto Ortega-Olmedo | 6-3,6-3 |
| ITF M25 Bakio | 2019/07/02 12:15 | Hendrik Jebens v David E Manogue | 6-3,6-4 |
| ITF M25 Bakio | 2019/07/01 13:30 | Hendrik Jebens v Jorge Mendieta | 6-2,6-1 |
| ITF M25 Martos | 2019/06/18 09:55 | Benjamin Winter Lopez v Hendrik Jebens | 6-4,6-4 |
| ITF M25 Martos | 2019/06/17 14:30 | Javier Molino v Hendrik Jebens | 4-6,3-6 |
| ITF M15 Majadahonda | 2019/05/28 08:00 | Luis Faria v Hendrik Jebens | 6-4,4-6,10-5 |
| ITF M15 Majadahonda | 2019/05/27 08:00 | Mikel Martinez v Hendrik Jebens | 3-6,4-6 |
| ITF M25 Vic | 2019/05/22 11:30 | Hendrik Jebens v Facundo Diaz Acosta | 3-6,3-6 |
| ITF M25 Vic | 2019/05/21 08:00 | Anton Desyatnik v Hendrik Jebens | 1-6,1-6 |