Round: 26 Ground: Hardcourt outdoor
| USA F34, Singles | 2016/10/25 18:30 | Michael Geerts v Santiago, Mico | 2-6,2-6 |
| USA F33, Singles | 2016/10/19 20:05 | Smith, Austin v Santiago, Mico | 6-1,6-1 |
| Fairfield, USA, Qualifications | 2016/10/08 21:35 | Santiago, Mico v Nevolo, Dennis | 3-6,3-6 |
| Challenger Stockton Qual | 2016/10/02 17:50 | Santiago, Mico v Bester, Philip | 3-6,1-6 |
| Challenger Stockton Qual | 2016/10/01 19:30 | Santiago, Mico v Watson, Ross | 6-2,6-1 |
| ITF USA F25 Qual | 2016/07/25 16:50 | Santiago, Mico v Goldin, Grayson M. | 1-6,2-6 |
| ITF USA F25 Qual | 2016/07/24 13:15 | Santiago, Mico v Race, Warren | 6-1,6-0 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Santiago, Mico v Donaldson, Brandon | 6-2,6-2 |
| 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 |
| 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 |