Round: 25 Ground: Hardcourt outdoor
| Challenger Fairfield Qual | 2016/10/08 18:50 | Michael Genender v Alexios Halebian | 6-7,4-6 |
| ITF USA F30 | 2016/09/27 16:00 | Miomir Kecmanovic v Alexios Halebian | 3-6,6-3,7-6 |
| ITF USA F29 | 2016/09/24 17:00 | Mackenzie McDonald v Alexios Halebian | 6-2,6-4 |
| ITF USA F29 | 2016/09/23 17:00 | Santiago Rodriguez Taverna v Alexios Halebian | 6-4,1-6,2-6 |
| ITF USA F29 | 2016/09/22 18:55 | Nicolas Moreno De Alboran v Alexios Halebian | 3-6,4-6 |
| ITF USA F29 | 2016/09/20 18:50 | Florent Diep v Alexios Halebian | 6-4,2-6,0-6 |
| ITF USA F28 | 2016/09/16 17:00 | Sebastian Fanselow v Alexios Halebian | 7-5,6-4 |
| ITF USA F28 | 2016/09/15 17:00 | Guus Koevermans v Alexios Halebian | 6-7,3-6 |
| Challenger Columbus | 2016/09/23 16:00 | Tennys Sandgren v Roberto Quiroz | 6-0,7-6 |
| Challenger Columbus | 2016/09/21 16:50 | Roberto Quiroz v Evan King | 6-4,6-4 |
| Challenger Columbus | 2016/09/20 15:00 | Roberto Quiroz v Brydan Klein | 6-4,6-2 |
| Challenger Columbus Qual | 2016/09/19 16:45 | Roberto Quiroz v Luke Bambridge | 6-4,6-4 |
| Challenger Columbus Qual | 2016/09/18 18:00 | Roberto Quiroz v Skander Mansouri | 6-4,6-1 |
| Challenger Cary | 2016/09/13 21:40 | Eric Quigley v Roberto Quiroz | 7-5,6-3 |
| Challenger Barranquilla | 2016/09/08 17:00 | Jose Hernandez-Fernandez v Roberto Quiroz | 7-6,4-6,6-2 |
| Challenger Barranquilla | 2016/09/06 15:30 | Roberto Quiroz v Darian King | 0-6,6-3,6-2 |