Round: 25 Ground: Clay
| 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 Sweden F4 | 2016/09/29 08:00 | Markus Eriksson v Dzmitry Zhyrmont | 4-6,6-3,4-6 |
| ITF Sweden F4 | 2016/09/28 08:00 | Jonathan Mridha v Dzmitry Zhyrmont | 4-6,4-6 |
| ITF Sweden F4 | 2016/09/26 09:00 | Marcus Mansson v Dzmitry Zhyrmont | 6-7,6-7 |
| ATP St Petersburg Qual | 2016/09/18 12:00 | Radu Albot v Dzmitry Zhyrmont | 6-2,4-6,6-4 |
| ITF Estonia F1 | 2015/11/09 08:00 | Vitaly Kozyukov v Kristofer Siimar | 6-2,6-3 |
| ITF Estonia F3 | 2015/11/03 15:00 | Kenneth Raisma v Kristofer Siimar | 6-2,6-0 |
| ITF Lithuania F1 | 2015/07/21 10:25 | Claudio Fortuna v Kristofer Siimar | 7-5,6-0 |
| ITF Estonia F2 | 2014/07/19 07:00 | Kristofer Siimar v Kirill Saplin | 5-7,1-6 |
| ITF Estonia F1 | 2014/07/13 07:00 | Julius Tverijonas v Kristofer Siimar | 4-6,6-4,6-2 |