Stadium: COURT 2 Round: 46 Ground: Hardcourt outdoor
| Monterrey, Mexico | 2016/10/12 18:00 | Denis Kudla v Ortega-Olmedo, Roberto | 6-3,6-3 |
| Monterrey, Mexico | 2016/10/10 19:40 | Ortega-Olmedo, Roberto v Lizariturry, Juan | 6-3,6-1 |
| Others | 2016/09/24 12:55 | Yann Marti v Ortega-Olmedo, Roberto | 6-7,7-6,6-1 |
| ATP Metz Qual | 2016/09/18 13:30 | Ortega-Olmedo, Roberto v Constant Lestienne | 3-6,6-3,1-6 |
| Challenger Seville | 2016/09/06 11:00 | Ortega-Olmedo, Roberto v Taro Daniel | 1-6,4-6 |
| Seville, Spain, Qualifying | 2016/09/04 09:00 | Ortega-Olmedo, Roberto v Toledo Bague, Pol | 6-4,5-7,1-6 |
| Seville, Spain, Qualifying | 2016/09/03 15:10 | Ortega-Olmedo, Roberto v Ribeiro Navarrete, Samuel | 6-2,6-1 |
| Seville, Spain, Qualifying | 2016/09/03 15:05 | Ortega-Olmedo, Roberto v Samuel R. Navarrete | 6-2,6-1 |
| Challenger Las Vegas Qual | 2016/10/15 19:50 | Hendrik Jebens v Courtney John Lock | 7-5,6-2 |
| Fairfield, USA, Qualifications | 2016/10/08 17:00 | Glasspool, Lloyd v Hendrik Jebens | 6-3,6-7,7-6 |
| ITF USA F30 | 2016/09/24 20:00 | Hendrik Jebens v Tristan Boyer | 1-6,1-6 |
| ITF USA F29 | 2016/09/19 18:30 | Brymer, Gage v Hendrik Jebens | 6-2,6-3 |
| ITF USA F29 | 2016/09/18 18:00 | Jacob Brumm v Hendrik Jebens | 4-6,4-6 |
| ITF USA F29 | 2016/09/17 20:00 | Tebet Filho, Marcelo v Hendrik Jebens | 6-4,4-6,1-6 |
| ITF USA F29 | 2016/09/16 23:00 | Marquez, Joaquin v Hendrik Jebens | 2-6,3-6 |
| ITF USA F28 | 2016/09/13 18:30 | Hendrik Jebens v Halebian, Alexios | 6-7,6-4,2-6 |