Round: 27 Ground: Hardcourt outdoor
| Porto Rico F1, Simples | 2016/12/21 13:30 | Thai-Son Kwiatkowski v Isaiah Strode | 6-3,6-2 |
| Porto Rico F1, Simples | 2016/12/19 14:00 | Thai-Son Kwiatkowski v Grovas, Rafael E | 6-2,6-1 |
| Challenger Charlottesville | 2016/11/01 20:50 | Smyczek, Tim v Thai-Son Kwiatkowski | 6-4,2-6,6-3 |
| Charlottesville, USA, Qualifying | 2016/10/31 16:10 | Thai-Son Kwiatkowski v Garanganga, Takanyi | 6-4,6-3 |
| Charlottesville, USA, Qualifying | 2016/10/30 18:05 | Libietis, Mikelis v Thai-Son Kwiatkowski | 2-6,3-6 |
| Charlottesville, USA, Qualifying | 2016/10/29 20:10 | Williams, Rhyne v Thai-Son Kwiatkowski | 7-6,3-6,1-6 |
| US Open, New York, USA, Qualifying | 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 |
| Porto Rico F1, Simples | 2016/12/21 13:30 | Hu, Nicholas S v Kirkov, Vasil | 1-6,6-7 |
| Porto Rico F1, Simples | 2016/12/19 16:25 | Kirkov, Vasil v Santanna, B. | 7-5,5-7,6-2 |
| ITF USA F37 | 2016/11/13 17:00 | Kirkov, Vasil v Lin, Jack Mingjie | 4-6,0-6 |
| ITF USA F36 | 2016/11/08 15:30 | Kirkov, Vasil v Spencer, Wil | 1-6,3-6 |
| US Open, New York, USA, Qualifying | 2016/08/23 15:00 | Kirkov, Vasil v Reuter, Yannik | 2-6,5-7 |
| ITF USA F25 | 2016/07/27 14:00 | Kirkov, Vasil v King, Evan | 4-6,2-6 |
| ITF USA F25 Qual | 2016/07/25 15:00 | Kirkov, Vasil v Kumar, Sameer | 6-4,6-4 |
| ITF USA F25 Qual | 2016/07/23 13:30 | Kirkov, Vasil v Alafia Ayeni | 6-2,6-4 |