Round: 26 Ground: Hardcourt indoor
| ITF Estonia F4 | 2016/11/07 23:00 | Ivanov, Vladimir v Sekulic, Milos | 3-6,7-5,7-6 |
| ITF Estonia F3 | 2016/11/04 13:25 | Niels Lootsma v Ivanov, Vladimir | 7-5,6-3 |
| ITF Estonia F3 | 2016/11/03 14:50 | Beck, Karol v Ivanov, Vladimir | 3-6,5-7 |
| ITF Estonia F3 | 2016/11/01 13:25 | Siimar, Kristofer v Ivanov, Vladimir | 0-6,4-6 |
| ITF Estonia F2 | 2016/10/30 10:00 | Ivanov, Vladimir v Kenneth Raisma | 4-6,3-6 |
| ITF Estonia F2 | 2016/10/29 09:00 | Zhyrmont, Dzmitry v Ivanov, Vladimir | 3-6,7-6,2-6 |
| 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 F4 | 2016/11/07 23:00 | Khomentovskiy, Matvey v Davydov, Ivan | 7-6,6-1 |
| ITF Estonia F4 | 2016/11/04 23:00 | Khomentovskiy, Matvey v Irdoja, Oskar | 6-1,6-0 |
| ITF Germany F17 | 2016/10/31 09:00 | Khomentovskiy, Matvey v Bertsch, Jochen | 6-3,3-6,2-6 |
| ITF Germany F15 | 2016/10/20 12:30 | Khomentovskiy, Matvey v Jurij Rodionov | 6-3,5-7,6-7 |
| ITF Germany F15 | 2016/10/18 09:00 | David Pichler v Khomentovskiy, Matvey | 6-4,4-6,5-7 |
| ITF Germany F15 | 2016/10/16 11:00 | Khomentovskiy, Matvey v Mrazek, David | 6-1,3-6,6-1 |
| ITF Germany F14 | 2016/10/12 10:00 | Khomentovskiy, Matvey v Louis Wessels | 2-6,2-6 |
| ITF Germany F14 | 2016/10/10 10:00 | Khomentovskiy, Matvey v Born, Yannick Stephan | 3-6,6-3,7-6 |