Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger Vicenza | 2019/05/30 16:50 | Julian Ocleppo v Gianluca Mager | 4-6,7-5,6-7 |
| Challenger Vicenza | 2019/05/28 09:40 | Kenny de Schepper v Julian Ocleppo | 0-6,4-6 |
| Challenger Jerusalem | 2019/05/22 10:25 | Julian Ocleppo v John-Patrick Smith | 6-7,5-7 |
| Challenger Jerusalem | 2019/05/21 08:25 | Yshai Oliel v Julian Ocleppo | 6-7,2-6 |
| Challenger Jerusalem | 2019/05/20 07:00 | Julian Ocleppo v Yair Sarouk | 6-1,6-4 |
| Challenger Rome | 2019/05/06 15:00 | Mate Valkusz v Julian Ocleppo | 6-2,6-2 |
| Challenger Ostrava | 2019/04/29 08:00 | Enrico Dalla Valle v Julian Ocleppo | 6-2,6-2 |
| Challenger Francavilla | 2019/04/23 14:20 | Julian Ocleppo v Rudolf Molleker | 4-6,6-3,4-6 |
| Challenger Jerusalem | 2019/05/23 07:00 | Brayden Schnur v Roberto Ortega-Olmedo | 6-3,6-3 |
| Challenger Samarkand | 2019/05/17 06:00 | Roberto Ortega-Olmedo v Sumit Nagal | 5-7,4-6 |
| Challenger Samarkand | 2019/05/16 09:05 | Lucas Miedler v Roberto Ortega-Olmedo | 6-7,2-6 |
| Challenger Samarkand | 2019/05/15 05:30 | Sergey Fomin v Roberto Ortega-Olmedo | 4-6,3-6 |
| Challenger Puerto Vallarta | 2019/04/29 19:45 | Roberto Ortega-Olmedo v Yusuke Takahashi | 5-7,1-6 |
| Challenger Leon | 2019/04/23 20:00 | Pedja Krstin v Roberto Ortega-Olmedo | 7-6,6-3 |
| Challenger Leon | 2019/04/22 17:30 | Roberto Ortega-Olmedo v Yusuke Takahashi | 6-4,6-4 |
| Challenger San Luis Potosi | 2019/04/17 20:25 | Pedro Sakamoto v Roberto Ortega-Olmedo | 6-4,6-2 |