Round: 27 Ground: Clay
| ITF - Ukraine F3 | 2016/05/25 07:00 | Denys Mylokostov v Gleb Alekseenko | 6-4,6-3 |
| ITF - Ukraine F3 | 2016/05/23 09:30 | Johan Sebastien Tatlot v Denys Mylokostov | 3-6,4-6 |
| ITF - Ukraine F2 | 2016/05/20 11:30 | Kamil Majchrzak v Denys Mylokostov | 6-1,6-1 |
| ITF - Ukraine F2 | 2016/05/19 08:00 | Denys Mylokostov v Vadim Alekseenko | 7-6,1-6,6-4 |
| ITF - Ukraine F1 | 2016/05/11 08:05 | Denys Mylokostov v Antoine Bellier | 3-6,6-7 |
| ITF - Ukraine F1 | 2016/05/09 11:30 | Bjoern Petersen v Denys Mylokostov | 3-6,3-6 |
| ITF - Indonesien F5 | 2015/12/22 07:30 | Denys Mylokostov v Franjo Raspudic | 4-6,0-6 |
| ITF - Tunesien F36 | 2015/12/18 09:00 | Ronan Joncour v Denys Mylokostov | 6-3,6-1 |
| ITF - Ukraine F3 | 2016/05/25 14:35 | Davide Galoppini v Vladimir Ivanov | 6-3,6-7,3-6 |
| ITF - Ukraine F3 | 2016/05/24 07:00 | Vitalii Shcherba v Vladimir Ivanov | 5-7,0-6 |
| ITF - Ukraine F2 | 2016/05/20 10:30 | Vladimir Ivanov v Antoine Bellier | 2-6,2-6 |
| ITF - Ukraine F2 | 2016/05/19 12:00 | Vladimir Ivanov v Alexander Lebedyn | 3-6,6-4,6-2 |
| ITF - Ukraine F2 | 2016/05/18 08:00 | Vladimir Ivanov v Vasko Mladenov | 6-3,6-2 |
| ITF - Kasachstan F4 | 2016/04/26 10:30 | Vladimir Ivanov v Markos Kalovelonis | 3-6,2-6 |
| ITF - Kasachstan F3 - Qualifikation | 2016/04/20 06:30 | Vladimir Ivanov v Stanislav Poplavskyy | 5-7,5-7 |
| Davis Cup | 2016/03/03 14:00 | Vladimir Ivanov v Granit Bajraliu | 6-0,6-2 |