Ground: Clay
| Challenger Meerbusch | 2016/08/15 14:00 | Jahn, Jeremy v Ortega-Olmedo, Roberto | 5-7,6-3,6-3 |
| ITF Italy F23 | 2016/08/03 10:10 | Ortega-Olmedo, Roberto v Wilson Leite | 3-6,2-6 |
| ITF Italy F23 | 2016/08/01 13:55 | Ortega-Olmedo, Roberto v Ghedin, Nicola | 6-3,4-6,6-1 |
| Segovia, Spain | 2016/07/27 16:00 | Kenny de Schepper v Ortega-Olmedo, Roberto | 6-3,6-3 |
| Segovia, Spain | 2016/07/25 11:00 | Horansky, Filip v Ortega-Olmedo, Roberto | 1-6,3-6 |
| Challenger Recanati | 2016/07/19 19:55 | Andrey Rublev v Ortega-Olmedo, Roberto | 6-2,6-4 |
| ATP Hamburg Qual | 2016/07/09 10:00 | Ortega-Olmedo, Roberto v Mertl, Jan | 4-6,2-6 |
| ITF Egypt F13 | 2016/07/02 17:45 | Aldin Setkic v Ortega-Olmedo, Roberto | 6-3,6-4 |
| Seville, Spain, Qualifying | 2016/09/03 08:55 | Lourenco, Diogo v Samuel R. Navarrete | 3-6,6-2,6-6 |