Round: 28 Ground: Clay
| ITF - Estónia F2 | 2016/10/28 11:00 | Dzmitry Zhyrmont v Patrik Fabian | 6-3,6-3 |
| ITF - Estónia F2 | 2016/10/26 13:00 | Dzmitry Zhyrmont v Kristjan Tamm | 6-3,4-6,6-3 |
| ITF - Estónia F2 | 2016/10/24 15:00 | Dzmitry Zhyrmont v Kristofer Siimar | 6-0,6-0 |
| ATP - Moscovo - Qualificação | 2016/10/15 13:00 | Dzmitry Zhyrmont v Federico Gaio | 6-7,3-6 |
| ITF - Suécia F5 | 2016/10/04 16:15 | Andriej Kapas v Dzmitry Zhyrmont | 6-1,3-6,6-3 |
| ITF - Suécia F4 | 2016/10/01 09:00 | Edward Corrie v Dzmitry Zhyrmont | 6-7,1-6 |
| ITF - Suécia F4 | 2016/09/30 08:00 | Sam Barry v Dzmitry Zhyrmont | 2-6,3-6 |
| ITF - Suécia F4 | 2016/09/29 08:00 | Markus Eriksson v Dzmitry Zhyrmont | 4-6,6-3,4-6 |
| ITF - Estónia F2 | 2016/10/28 12:30 | Vladimir Ivanov v Andrea Basso | 6-2,6-4 |
| ITF - Estónia F2 | 2016/10/27 13:00 | Vladimir Ivanov v Oskar Lusti | 6-0,6-0 |
| ITF - Estónia F2 | 2016/10/25 09:20 | Vladimir Ivanov v Shahar Elbaz | 6-1,6-0 |
| Challenger Tashkent Qual | 2016/10/09 07:25 | Alexander Vasilenko v Vladimir Ivanov | 7-6,6-4 |
| Challenger Tashkent Qual | 2016/10/08 09:05 | Pavel Petrov v Vladimir Ivanov | 5-7,2-6 |
| ITF - Cazaquistão F7 | 2016/10/06 05:50 | Vladimir Ivanov v Alexander Igoshin | 6-4,6-7,0-6 |
| ITF - Cazaquistão F7 | 2016/10/05 05:15 | Vladimir Ivanov v Grigoriy Lomakin | 4-6,6-0,6-1 |
| ITF - Cazaquistão F6 | 2016/10/01 04:00 | Vladimir Ivanov v Sanjar Fayziev | 6-4,3-6,2-6 |