Round: 27 Ground: Carpet indoor
| ITF Russia F8 | 2016/09/09 08:00 | Dzmitry Zhyrmont v Alexander Vasilenko | 4-6,6-3,3-6 |
| ITF Estonia F3 | 2014/10/30 10:00 | Alexander Vasilenko v Dzmitry Zhyrmont | 3-6,4-6 |
| ITF Estonia F3 | 2016/11/02 15:20 | Dzmitry Zhyrmont v Shane Vinsant | 6-4,6-2 |
| 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 Mosca - Qual. | 2016/10/15 13:00 | Dzmitry Zhyrmont v Federico Gaio | 6-7,3-6 |
| ITF Svezia F5 | 2016/10/04 16:15 | Andriej Kapas v Dzmitry Zhyrmont | 6-1,3-6,6-3 |
| ITF Svezia F4 | 2016/10/01 09:00 | Edward Corrie v Dzmitry Zhyrmont | 6-7,1-6 |
| ITF Estonia F3 | 2016/11/03 12:00 | Alexander Vasilenko v Kenneth Raisma | 7-6,3-6,6-3 |
| ITF Estonia F3 | 2016/11/01 12:05 | Alexander Vasilenko v Mattias Siimar | 6-1,6-3 |
| ITF Estonia F2 | 2016/10/27 11:00 | Alexander Vasilenko v Mark Whitehouse | 5-7,6-7 |
| ITF Estonia F2 | 2016/10/25 13:00 | Alexander Vasilenko v Anton Pavlov | 6-4,7-5 |
| Challenger Tashkent | 2016/10/11 06:50 | Alexander Vasilenko v Denys Molchanov | 6-7,6-7 |
| Challenger Tashkent Qual | 2016/10/10 05:00 | Marcelo Demoliner v Alexander Vasilenko | 4-6,4-6 |
| Challenger Tashkent Qual | 2016/10/09 07:25 | Alexander Vasilenko v Vladimir Ivanov | 7-6,6-4 |
| Challenger Tashkent Qual | 2016/10/08 09:30 | Alexander Vasilenko v Gero Kretschmer | 7-6,6-3 |