Round: 29 Ground: Hardcourt outdoor
| ITF Puerto Rico F1 | 2016/12/23 16:10 | Alexios Halebian v Benjamin Lock | 6-2,7-6 |
| ITF Puerto Rico F1 | 2016/12/22 14:00 | Evan King v Alexios Halebian | 6-7,6-7 |
| ITF Puerto Rico F1 | 2016/12/21 15:25 | Nebojsa Peric v Alexios Halebian | 0-6,1-6 |
| ITF Puerto Rico F1 | 2016/12/20 13:30 | Richard Torres v Alexios Halebian | 2-6,4-6 |
| ITF Dominican Rep F3 | 2016/12/13 13:30 | Alexios Halebian v Ivan Endara | 4-6,4-6 |
| ITF Dominican Republic F2 | 2016/12/05 14:30 | Victor Ouvrard v Alexios Halebian | 6-3,6-7,7-6 |
| ITF USA F39 | 2016/11/30 19:00 | Alexios Halebian v Tim Van Rijthoven | 5-7,6-1,1-6 |
| ITF USA F39 | 2016/11/29 22:50 | Mico Santiago v Alexios Halebian | 3-6,6-4,6-7 |
| ITF Puerto Rico F1 | 2016/12/23 14:00 | Brayden Schnur v Thai-Son Kwiatkowski | 6-4,2-6,0-6 |
| ITF Puerto Rico F1 | 2016/12/22 16:20 | Thai-Son Kwiatkowski v Vasil Kirkov | 6-1,6-3 |
| ITF Puerto Rico F1 | 2016/12/21 13:30 | Thai-Son Kwiatkowski v Isaiah Strode | 6-3,6-2 |
| ITF Puerto Rico F1 | 2016/12/19 14:00 | Thai-Son Kwiatkowski v Rafael E. Grovas | 6-2,6-1 |
| Challenger Charlottesville | 2016/11/01 20:50 | Tim Smyczek v Thai-Son Kwiatkowski | 6-4,2-6,6-3 |
| Challenger Charlottesville Qual | 2016/10/31 16:10 | Thai-Son Kwiatkowski v Takanyi Garanganga | 6-4,6-3 |
| Challenger Charlottesville Qual | 2016/10/30 18:05 | Mikelis Libietis v Thai-Son Kwiatkowski | 2-6,3-6 |
| Challenger Charlottesville Qual | 2016/10/29 20:10 | Rhyne Williams v Thai-Son Kwiatkowski | 7-6,3-6,1-6 |