Round: 25 Ground: Carpet indoor
| ITF Estonia F2 | 2016/10/24 15:00 | Dzmitry Zhyrmont v Kristofer Siimar | 6-0,6-0 |
| 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 |
| ITF Estonia F2 | 2016/10/30 10:00 | Vladimir Ivanov v Kenneth Raisma | 4-6,3-6 |
| 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 12:30 | Vladimir Ivanov v Andrea Basso | 6-2,6-4 |
| ITF Estonia F2 | 2016/10/27 13:00 | Vladimir Ivanov v Oskar Lusti | 6-0,6-0 |
| ITF Estonia 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 Kazakhstan F7 | 2016/10/06 05:50 | Vladimir Ivanov v Alexander Igoshin | 6-4,6-7,0-6 |