Round: 60 Ground: Clay
| ITF USA F14 | 2016/04/17 14:30 | Juan Manuel Benitez Chavarriaga v Jared Thompkins | 6-0,6-2 |
| 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 F14 | 2016/04/17 14:30 | Rowland Phillips v Pietro Rimondini | 2-6,6-7 |
| ITF USA F9 Qual | 2016/02/27 16:00 | Gonzales Austin v Pietro Rimondini | 6-3,6-4 |
| ITF USA F7 Qual | 2016/02/15 17:00 | Pietro Rimondini v Junior Alexander Ore | 1-6,4-6 |
| ITF USA F7 Qual | 2016/02/14 17:00 | Augusto Laranja v Pietro Rimondini | 7-6,4-6,1-6 |
| ITF USA F7 Qual | 2016/02/12 16:00 | Brian Cernoch v Pietro Rimondini | 6-7,7-5,3-6 |
| ITF USA F5 | 2016/01/26 15:00 | Pietro Rimondini v Pedro Sakamoto | 4-6,3-6 |
| ITF USA F4 | 2016/01/19 16:30 | Pietro Rimondini v Sekou Bangoura | 4-6,5-7 |
| ITF USA F3 Qual | 2016/01/11 17:00 | Alfredo Perez v Pietro Rimondini | 6-2,6-1 |