Round: 45 Ground: Hardcourt indoor
| Challenger Cary Qual | 2016/09/10 15:50 | Carter, Andrew v Uspensky, Dennis | 6-2,6-4 |
| ITF Spain F25 | 2016/08/10 08:30 | Alejandro Davidovich Fokina v Uspensky, Dennis | 6-1,6-2 |
| ITF Spain F25 | 2016/08/08 15:00 | Fernandez Labarta, Luis v Uspensky, Dennis | 1-6,2-6 |
| ITF Spain F24 | 2016/08/04 15:00 | Uspensky, Dennis v Artunedo Martinav. | 2-6,1-6 |
| ITF Spain F24 | 2016/08/03 15:00 | Nicolas Alvarez Varona v Uspensky, Dennis | 3-6,6-7 |
| ITF Spain F24 | 2016/08/01 14:00 | Uspensky, Dennis v Montes, Dario | 6-3,6-4 |
| ITF Canada F5 | 2016/07/07 18:00 | Blake Mott v Uspensky, Dennis | 6-1,4-6,7-6 |
| ITF Canada F5 | 2016/07/05 17:30 | Uspensky, Dennis v Sood, Chandril | 7-5,6-2 |
| ITF Finland F3 | 2016/08/16 22:00 | Pollanen, Herkko v von Massow, George | 3-6,6-1,6-7 |
| ITF Finland F3 | 2016/08/15 22:00 | Gohlke, Delf v Pollanen, Herkko | 4-6,3-6 |
| ITF Finland F3 Qual | 2016/08/13 22:00 | Gohlke, Delf v Pollanen, Herkko | 3-6,1-6 |
| ITF Finland F3 Qual | 2016/08/12 22:00 | Saatela, Leevi v Pollanen, Herkko | 3-6,1-6 |
| ITF Finland F2 Qual | 2016/08/06 10:00 | Pollanen, Herkko v Wennakoski, Max | 4-6,7-5,2-6 |
| ITF Finland F1 | 2016/08/03 10:50 | Thai-Son Kwiatkowski v Pollanen, Herkko | 6-3,6-2 |
| ITF Finland F1 | 2016/08/02 09:40 | Barros, Emmanuel v Pollanen, Herkko | 2-6,1-6 |
| ITF Estonia F1 | 2016/07/26 22:00 | Arreche, Nicolas Alberto v Pollanen, Herkko | 1-6,6-1,6-1 |