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