Round: 27 Ground: Hardcourt outdoor
| ITF Spain F36 | 2016/11/10 09:00 | Monteiro, Joao v Raul Brancaccio | 6-4,1-6,6-2 |
| ITF Spain F36 | 2016/11/09 10:40 | Monteiro, Joao v Syromolotov Netrebin, Yuri | 6-1,6-3 |
| ITF Tunisia F28 | 2016/10/22 08:30 | Monteiro, Joao v Grigelis, Laurynas | 3-6,4-6 |
| ITF Tunisia F28 | 2016/10/21 13:25 | Monteiro, Joao v Mora, Maxime | 6-0,6-4 |
| ITF Tunisia F28 | 2016/10/20 14:00 | Geens, Clement v Monteiro, Joao | 7-6,4-6,1-6 |
| ITF Tunisia F28 | 2016/10/19 08:30 | Dmitriev, Kirill v Monteiro, Joao | 7-6,2-6,3-6 |
| ITF Tunisia F27 | 2016/10/12 12:40 | Marti, Javier v Monteiro, Joao | 6-2,6-4 |
| ITF Portugal F12 | 2016/10/05 09:15 | Lorenzo Giustino v Monteiro, Joao | 6-4,6-2 |
| ITF Spain F36 | 2016/11/10 09:00 | Benjamin Pietri v Ortega-Olmedo, Roberto | 2-6,1-6 |
| ITF Spain F36 | 2016/11/09 09:00 | Mardones, Bruno v Ortega-Olmedo, Roberto | 4-6,1-6 |
| USA F34, Singles | 2016/10/27 19:30 | Santiago, Mico v Ortega-Olmedo, Roberto | 6-2,6-4 |
| USA F34, Singles | 2016/10/25 18:15 | Smith, Austin v Ortega-Olmedo, Roberto | 2-6,6-4,1-6 |
| Challenger Las Vegas | 2016/10/19 19:35 | Giraldo, Santiago v Ortega-Olmedo, Roberto | 6-3,6-2 |
| Challenger Las Vegas Qual | 2016/10/17 17:30 | Ortega-Olmedo, Roberto v Escobar, Gonzalo | 6-3,2-6,6-4 |
| Challenger Las Vegas Qual | 2016/10/16 19:45 | Ortega-Olmedo, Roberto v Hendrik Jebens | 6-0,6-1 |
| Monterrey, Mexico | 2016/10/12 18:00 | Denis Kudla v Ortega-Olmedo, Roberto | 6-3,6-3 |