Round: 25 Ground: Clay
| ITF USA F7 Qual | 2016/02/15 17:00 | Juan Manuel Benitez Chavarriaga v Damon Gooch | 6-2,6-7,6-2 |
| ITF USA F19 | 2016/06/16 18:15 | Juan Manuel Benitez Chavarriaga v Tigre Hank | 6-3,6-7,2-6 |
| ITF USA F19 | 2016/06/14 15:00 | Carlos Ramirez Utermann v Juan Manuel Benitez Chavarriaga | 2-6,0-6 |
| ITF Mexico F3 | 2016/05/20 20:00 | Juan Manuel Benitez Chavarriaga v Adam El Mihdawy | 4-6,5-7 |
| ITF Mexico F3 | 2016/05/19 15:00 | Juan Manuel Benitez Chavarriaga v Michael-Ray Pallares-Gonzalez | 7-5,6-3 |
| ITF Mexico F3 | 2016/05/17 18:55 | Mauricio Echazu v Juan Manuel Benitez Chavarriaga | 4-6,6-2,5-7 |
| ITF Mexico F3 | 2016/05/16 15:00 | Juan Manuel Benitez Chavarriaga v Sergio Luis H Ramirez | 6-3,1-6,6-2 |
| ITF Mexico F3 | 2016/05/15 17:30 | Juan Manuel Benitez Chavarriaga v Alonso A Delgado | 6-1,6-2 |
| ITF Mexico F2 | 2016/05/13 16:45 | Adam El Mihdawy v Juan Manuel Benitez Chavarriaga | 7-5,4-6,6-3 |
| ITF USA F18 | 2016/06/15 17:45 | Damon Gooch v Rubin Statham | 6-7,4-6 |
| ITF USA F17 | 2016/06/09 13:00 | Thai-Son Kwiatkowski v Damon Gooch | 6-0,6-3 |
| ITF USA F17 | 2016/06/07 15:15 | Damon Gooch v Sekou Bangoura | 2-6,6-1,6-3 |
| ITF USA F17 Qual | 2016/06/06 13:00 | Damon Gooch v Hendrik Jebens | 6-4,6-2 |
| ITF USA F17 Qual | 2016/06/05 13:00 | Damon Gooch v Tyler Mercier | 6-2,6-2 |
| ITF USA F16 | 2016/05/03 13:00 | Mico Santiago v Damon Gooch | 6-4,6-3 |
| Challenger Drummondville Qual | 2016/03/14 16:00 | Tim Van Rijthoven v Damon Gooch | 6-2,6-2 |
| Challenger Drummondville Qual | 2016/03/13 17:45 | Damon Gooch v Kaichi Uchida | 6-4,5-7,6-2 |