Round: 60 Ground: Clay
| ITF USA F14 | 2016/04/18 15:00 | Juan Manuel Benitez Chavarriaga v Aron Pierce | 6-2,6-1 |
| ITF USA F15 Qual | 2016/04/23 17:00 | Juan Manuel Benitez Chavarriaga v Brian Battistone | 6-1,6-4 |
| ITF USA F14 | 2016/04/21 14:00 | Patrick Daciek v Juan Manuel Benitez Chavarriaga | 6-3,6-1 |
| ITF USA F14 | 2016/04/20 17:15 | Juan Manuel Benitez Chavarriaga v Evan Song | 6-2,7-6 |
| ITF USA F14 | 2016/04/18 15:00 | Juan Manuel Benitez Chavarriaga v Aron Pierce | 6-2,6-1 |
| 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 F15 Qual | 2016/04/22 17:00 | Aron Pierce v Geronimo E Busleiman | 6-7,6-2,6-4 |
| ITF USA F14 | 2016/04/18 15:00 | Juan Manuel Benitez Chavarriaga v Aron Pierce | 6-2,6-1 |
| ITF USA F14 | 2016/04/17 20:30 | Sean Burnette v Aron Pierce | 3-6,6-1,5-7 |
| ITF USA F14 | 2016/04/17 15:00 | Aron Pierce v Simon Navarro | 6-3,7-6 |
| ITF USA F31 Qual | 2015/10/31 15:00 | Jonathan Pearlman v Aron Pierce | 5-7,1-6 |
| ITF USA F29 | 2014/10/19 15:00 | Pablo Nunez v Aron Pierce | 6-7,6-3,2-6 |
| ITF USA F27 | 2014/10/08 22:00 | Aron Pierce v Naoki Nakagawa | 1-6,4-6 |
| ITF USA F27 Qual | 2014/10/04 18:00 | Aron Pierce v Brandon Donaldson | 6-3,6-4 |