Round: 25 Ground: Clay
| 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 Sweden F4 | 2016/09/28 08:00 | Jonathan Mridha v Zhyrmont, Dzmitry | 4-6,4-6 |
| ITF Sweden F4 | 2016/09/26 09:00 | Mansson, Marcus v Zhyrmont, Dzmitry | 6-7,6-7 |
| St. Petersburg, Russia, Qualifying | 2016/09/18 12:00 | Radu Albot v Zhyrmont, Dzmitry | 6-2,4-6,6-4 |
| ITF Estonia F1 | 2015/11/09 08:00 | Kozyukov, Vitaly v Siimar, Kristofer | 6-2,6-3 |
| ITF Estonia F3 | 2015/11/03 15:00 | Kenneth Raisma v Siimar, Kristofer | 6-2,6-0 |
| ITF Lithuania F1 | 2015/07/21 10:25 | Fortuna, Claudio v Siimar, Kristofer | 7-5,6-0 |
| ITF Estonia F2 | 2014/07/19 07:00 | Siimar, Kristofer v Saplin, Kirill | 5-7,1-6 |
| ITF Estonia F1 | 2014/07/13 07:00 | Tverijonas, Julius v Siimar, Kristofer | 4-6,6-4,6-2 |