Round: 26 Ground: Carpet indoor
| ITF Estonia F2 | 2016/10/29 09:00 | Dzmitry Zhyrmont v Vladimir Ivanov | 3-6,7-6,2-6 |
| ITF Estonia F2 | 2016/10/28 11:00 | Dzmitry Zhyrmont v Patrik Fabian | 6-3,6-3 |
| ITF Estonia F2 | 2016/10/26 13:00 | Dzmitry Zhyrmont v Kristjan Tamm | 6-3,4-6,6-3 |
| ITF Estonia F2 | 2016/10/24 15:00 | Dzmitry Zhyrmont v Kristofer Siimar | 6-0,6-0 |
| ATP Moscow Qual | 2016/10/15 13:00 | Dzmitry Zhyrmont v Federico Gaio | 6-7,3-6 |
| ITF Sweden F5 | 2016/10/04 16:15 | Andriej Kapas v Dzmitry Zhyrmont | 6-1,3-6,6-3 |
| ITF Sweden F4 | 2016/10/01 09:00 | Edward Corrie v Dzmitry Zhyrmont | 6-7,1-6 |
| ITF Sweden F4 | 2016/09/30 08:00 | Sam Barry v Dzmitry Zhyrmont | 2-6,3-6 |
| ITF Estonia F3 | 2016/10/31 11:30 | Robertas Vrzesinski v Shane Vinsant | 2-6,1-6 |
| ITF Estonia F3 | 2016/10/30 09:00 | Shane Vinsant v Timur Kiyamov | 5-7,7-5,6-1 |
| ITF Estonia F3 | 2016/10/29 13:00 | Shane Vinsant v Ville-Petteri Ahti | 6-1,4-6,6-2 |
| ITF Estonia F2 | 2016/10/25 11:00 | Shane Vinsant v Andrea Basso | 3-6,7-6,3-6 |
| ITF USA F32 Qual | 2016/10/17 16:50 | Shane Vinsant v Jordi Arconada | 3-6,6-7 |
| ITF USA F31 Qual | 2016/10/09 14:00 | Hady Habib v Shane Vinsant | 6-3,6-4 |
| ITF USA F31 Qual | 2016/10/08 16:00 | Aron Pierce v Shane Vinsant | 3-6,6-2,4-6 |
| ITF USA F30 | 2016/09/28 18:05 | Takanyi Garanganga v Shane Vinsant | 6-2,6-1 |