Round: 60 Ground: Clay
| ITF USA F15 Qual | 2016/04/24 17:00 | Juan Manuel Benitez Chavarriaga v Aron Pierce | 6-3,6-1 |
| 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 |
| ITF USA F15 Qual | 2016/04/24 17:00 | Michael Lippens v Victor Krustev | 6-3,6-7,7-6 |
| ITF USA F15 Qual | 2016/04/23 18:00 | Michael Lippens v Jack Vance | 6-3,6-4 |
| ITF USA F4 | 2016/01/17 16:00 | Brian Battistone v Michael Lippens | 6-1,6-2 |
| ITF USA F3 | 2016/01/13 20:40 | Michael Lippens v Young Seok Kim | 6-3,3-6,4-6 |
| ITF USA F33 | 2015/11/18 17:45 | Michael Lippens v Gianni Ross | 3-6,6-7 |
| ITF USA F32 Qual | 2015/11/07 14:00 | Nick Chappell v Michael Lippens | 6-3,6-1 |
| ITF USA F25 Qual | 2015/08/08 14:00 | Michael Lippens v Konrad Zieba | 3-6,2-6 |
| ITF USA F24 Qual | 2015/08/02 15:00 | Michael Lippens v Strong Kirchheimer | 0-6,1-6 |