Round: 27 Ground: Hardcourt outdoor
| 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 |
| US Open Qual | 2016/08/23 16:55 | Henri Laaksonen v Thai-Son Kwiatkowski | 2-6,6-1,6-4 |
| ITF Finland F2 | 2016/08/12 12:00 | Thai-Son Kwiatkowski v Tallon Griekspoor | 6-4,4-6,5-7 |
| ITF Puerto Rico F1 | 2016/12/21 13:30 | Nicholas S. Hu v Vasil Kirkov | 1-6,6-7 |
| ITF Puerto Rico F1 | 2016/12/19 16:25 | Vasil Kirkov v Bruno Santanna | 7-5,5-7,6-2 |
| ITF USA F37 | 2016/11/13 17:00 | Vasil Kirkov v Jack Mingjie Lin | 4-6,0-6 |
| ITF USA F36 | 2016/11/08 15:30 | Vasil Kirkov v Wil Spencer | 1-6,3-6 |
| US Open Qual | 2016/08/23 15:00 | Vasil Kirkov v Yannik Reuter | 2-6,5-7 |
| ITF USA F25 | 2016/07/27 14:00 | Vasil Kirkov v Evan King | 4-6,2-6 |
| ITF USA F25 Qual | 2016/07/25 15:00 | Vasil Kirkov v Sameer Kumar | 6-4,6-4 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Vasil Kirkov v Alafia Ayeni | 6-2,6-4 |