Round: 60 Ground: Clay
| Challenger Sarasota Qual | 2016/04/11 16:40 | Juan Manuel Benitez Chavarriaga v Emilio Gomez | 3-6,2-6 |
| Challenger Sarasota Qual | 2016/04/10 18:25 | Robin Stanek v Juan Manuel Benitez Chavarriaga | 5-7,7-5,1-6 |
| Challenger Sarasota Qual | 2016/04/09 17:00 | Daniel Elahi Galan v Juan Manuel Benitez Chavarriaga | 2-6,6-7 |
| ITF USA F8 | 2016/02/25 16:00 | Juan Manuel Benitez Chavarriaga v Juan Pablo Ficovich | 2-6,7-5,4-6 |
| ITF USA F7 | 2016/02/19 17:00 | Juan Manuel Benitez Chavarriaga v Juan Carlos Saez | 6-7,1-6 |
| ITF USA F7 | 2016/02/18 16:00 | Caio Zampieri v Juan Manuel Benitez Chavarriaga | 3-6,3-6 |
| ITF USA F7 Qual | 2016/02/15 17:00 | Juan Manuel Benitez Chavarriaga v Damon Gooch | 6-2,6-7,6-2 |
| ITF USA F7 Qual | 2016/02/14 17:00 | Jorge Montero v Juan Manuel Benitez Chavarriaga | 1-6,1-6 |
| ITF USA F11 Qual | 2016/03/20 16:00 | Jared Thompkins v Tyler Hochwalt | 5-7,1-6 |
| ITF USA F10 Qual | 2016/03/12 17:00 | Raleigh Smith v Jared Thompkins | 6-2,6-0 |
| ITF USA F9 Qual | 2016/02/26 16:00 | Evan Bynoe v Jared Thompkins | 7-6,6-1 |
| ITF USA F8 Qual | 2016/02/19 20:00 | Piotr Zbroja v Jared Thompkins | 6-4,3-6,6-2 |
| ITF USA F2 Qual | 2016/01/09 18:00 | Alejandro Tabilo v Jared Thompkins | 6-1,6-1 |
| ITF USA F33 Qual | 2015/11/14 16:30 | Bruno Savi v Jared Thompkins | 6-3,6-2 |
| ITF USA F32 Qual | 2015/11/08 16:00 | Jared Thompkins v Denis Shapovalov | 1-6,0-6 |
| ITF USA F28 | 2015/09/26 20:00 | Strong Kirchheimer v Jared Thompkins | 6-3,6-2 |